Homesinorlando.forsale Search Results

$3,193,000

Welcome to this charming stately lakefront estate, a true gem straight from the pages of Southern Living—just minutes from Winter Park and the finest dining in Maitland, all on the serene shores of Lake Sybelia. From the moment you arrive, the large, inviting porch with it's charming swing beckons you into a home flooded with natural light and warm wood floors and a thoughtfully designed layout. The heart of this home is the expansive kitchen, seamlessly flowing into the family room and offering French doors that lead to a picturesque backyard. The downstairs primary suite provides a luxurious retreat, featuring large walk-in closets and a beautifully remodeled bathroom with a soaking tub and dual vanities. A private guest suite is conveniently located off the family room, offering its own entrance and separation from the rest of the home. Upstairs, you'll discover three generously-sized secondary bedrooms, a dedicated theater room, a private study, and a spacious bonus room complete with custom built-ins—perfect for play, work, or relaxation. Move right in as this home has not only been freshly repainted but all bathrooms have been remodeled and refreshed. Step outside to your personal private oasis, with no rear neighbors, where a newly remodeled pool with a sun shelf, stunning decking, and fire bowls set the perfect ambiance for both relaxation and entertaining. The lush side yard enhances the home's charm, while the boat dock provides the perfect spot to watch breathtaking sunsets or enjoy water sports on Lake Sybelia. This exceptional property offers the perfect blend of comfort, style, and lakeside living. Don’t miss the opportunity to make it your own!

5 Beds ⋅ 5 Baths ⋅ Northshore Estates SubDv. ⋅ 32751 Zip Code

Welcome to this charming stately lakefront estate, a true gem straight from the pages of Southern Living—just minutes from Winter Park and the finest dining in Maitland, all on the serene shores of Lake Sybelia. From the moment you arrive, the large, inviting porch with it's charming swing beckons you into a home flooded with natural light and warm wood floors and a thoughtfully designed layout. The heart of this home is the expansive kitchen, seamlessly flowing into the family room and offering French doors that lead to a picturesque backyard. The downstairs primary suite provides a luxurious retreat, featuring large walk-in closets and a beautifully remodeled bathroom with a soaking tub and dual vanities. A private guest suite is conveniently located off the family room, offering its own entrance and separation from the rest of the home. Upstairs, you'll discover three generously-sized secondary bedrooms, a dedicated theater room, a private study, and a spacious bonus room complete with custom built-ins—perfect for play, work, or relaxation. Move right in as this home has not only been freshly repainted but all bathrooms have been remodeled and refreshed. Step outside to your personal private oasis, with no rear neighbors, where a newly remodeled pool with a sun shelf, stunning decking, and fire bowls set the perfect ambiance for both relaxation and entertaining. The lush side yard enhances the home's charm, while the boat dock provides the perfect spot to watch breathtaking sunsets or enjoy water sports on Lake Sybelia. This exceptional property offers the perfect blend of comfort, style, and lakeside living. Don’t miss the opportunity to make it your own!

571 N Lake Sybelia Drive, Maitland

$390,000

This charming move in ready furnished (furniture valued at approx. $7,500) first-floor unit is situated in the highly desirable Maitland Harbour condominium complex, nestled in the heart of Maitland. This intimate and picturesque community is ideally located on Lake Maitland and offers access to the entire Winter Park Chain of Lakes. Recently fully remodeled, the unit features stylish décor, abundant natural light, and stunning views of the community pool and Lake Maitland. Every detail, from the fixtures to the window treatments, has been thoughtfully chosen to make this a truly move-in-ready home. The complex is beautifully landscaped with lush tropical foliage and oak trees, complemented by a refreshing lake breeze. Enjoy afternoons on the lake, where you can indulge in water skiing, fishing, kayaking. The unit also benefits from a new roof, a completed milestone inspection, and an up-to-date reserve study. Conveniently located, this property is adjacent to Fort Maitland Park, across from Lake Lily, and just a short distance from downtown Maitland, where you can enjoy the weekend farmers market. It is also minutes from Rollins College, the University of Central Florida, Full Sail University, and the vibrant historic district of Winter Park, known for its fine dining and boutique shopping along Park Avenue.

2 Beds ⋅ 2 Baths ⋅ Maitland Harbour Apts SubDv. ⋅ 32751 Zip Code

This charming move in ready furnished (furniture valued at approx. $7,500) first-floor unit is situated in the highly desirable Maitland Harbour condominium complex, nestled in the heart of Maitland. This intimate and picturesque community is ideally located on Lake Maitland and offers access to the entire Winter Park Chain of Lakes. Recently fully remodeled, the unit features stylish décor, abundant natural light, and stunning views of the community pool and Lake Maitland. Every detail, from the fixtures to the window treatments, has been thoughtfully chosen to make this a truly move-in-ready home. The complex is beautifully landscaped with lush tropical foliage and oak trees, complemented by a refreshing lake breeze. Enjoy afternoons on the lake, where you can indulge in water skiing, fishing, kayaking. The unit also benefits from a new roof, a completed milestone inspection, and an up-to-date reserve study. Conveniently located, this property is adjacent to Fort Maitland Park, across from Lake Lily, and just a short distance from downtown Maitland, where you can enjoy the weekend farmers market. It is also minutes from Rollins College, the University of Central Florida, Full Sail University, and the vibrant historic district of Winter Park, known for its fine dining and boutique shopping along Park Avenue.

1000 S Orlando Avenue Unit 4, Maitland

$245,000

Welcome to this charming first-floor 2-bedroom, 1.5-bathroom condominium located in the highly desirable Lake Maitland Terrace community. This inviting home features a living room and dining room adorned with elegant wood-look tile, creating a warm and stylish ambiance. Lake Maitland Terrace offers an array of top-notch amenities designed to enhance your lifestyle. Enjoy a refreshing swim in the lakeside pool, or relax in the clubhouse, which boasts a renovated kitchen and a screened porch with stunning views of Lake Maitland. Outdoor enthusiasts will appreciate the private dock, perfect for paddle boarding, and canoeing, with easy access to the Chain of Lakes. Additional community features include laundry facilities, putting greens, shuffleboard courts, assigned storage units, indoor bicycle storage, and a car wash station. The new metal roof, installed in 2023, provides added peace of mind. The community is professionally managed with an on-site manager and maintenance team, ensuring a well-maintained environment. The HOA covers essential services such as water, sewer, grounds maintenance, and valet garbage collection. For added convenience, mail is delivered directly to your door. Boat slips occasionally become available for residents at an additional cost. This condo is ideally situated near Maitland’s finest restaurants, shopping, and dining options. It is also just a short drive to downtown Orlando and Winter Park's Park Avenue. The location offers easy access to I-4, making commutes a breeze. Enjoy the convenience of walking to the Enzian Theater and Lake Lily, and being just a 5-minute drive from Winter Park’s vibrant downtown area. Experience the perfect blend of comfort, convenience, and community living in this delightful Lake Maitland Terrace condominium. Don't miss the opportunity to make this your new home.

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

Welcome to this charming first-floor 2-bedroom, 1.5-bathroom condominium located in the highly desirable Lake Maitland Terrace community. This inviting home features a living room and dining room adorned with elegant wood-look tile, creating a warm and stylish ambiance. Lake Maitland Terrace offers an array of top-notch amenities designed to enhance your lifestyle. Enjoy a refreshing swim in the lakeside pool, or relax in the clubhouse, which boasts a renovated kitchen and a screened porch with stunning views of Lake Maitland. Outdoor enthusiasts will appreciate the private dock, perfect for paddle boarding, and canoeing, with easy access to the Chain of Lakes. Additional community features include laundry facilities, putting greens, shuffleboard courts, assigned storage units, indoor bicycle storage, and a car wash station. The new metal roof, installed in 2023, provides added peace of mind. The community is professionally managed with an on-site manager and maintenance team, ensuring a well-maintained environment. The HOA covers essential services such as water, sewer, grounds maintenance, and valet garbage collection. For added convenience, mail is delivered directly to your door. Boat slips occasionally become available for residents at an additional cost. This condo is ideally situated near Maitland’s finest restaurants, shopping, and dining options. It is also just a short drive to downtown Orlando and Winter Park's Park Avenue. The location offers easy access to I-4, making commutes a breeze. Enjoy the convenience of walking to the Enzian Theater and Lake Lily, and being just a 5-minute drive from Winter Park’s vibrant downtown area. Experience the perfect blend of comfort, convenience, and community living in this delightful Lake Maitland Terrace condominium. Don't miss the opportunity to make this your new home.

1140 S Orlando Avenue Unit F-3, Maitland

$2,850,000

PRICE IMPROVEMENT!! New Construction with Winter Park Chain of Lakes Access!! You'll be stunned by this gorgeous coastal style home on a private canal that leads to Lake Maitland. This magnificent residence features 5 bedrooms, a bonus room, pool with a relaxing spa and brand new covered boat dock. Your journey begins in the grand two-story foyer featuring elegant lighting choices which are sure to impress. On the left is your study or flex space which can be used as a an additional bedroom as well. As you step into the generous and open grand room to your left is the elegant wine room. The open kitchen is a chef's dream featuring GE Cafe appliances , including a 36" freestanding range as well an Advantium oven and convection wall oven. Elegant slim shaker cabinetry and a large gathering island for entertaining complete this wonderful space. Off the kitchen is a scullery and laundry area with additional dishwasher and refrigerator for preparing grand holiday spreads. The dining room features an additional bar area with beverage refrigeration and overlooks the pool and canal so you can enjoy the views as you share a meal. Summers by the pool will be filled with grilling on the porch as you enjoy the lanai and days on the famed chain of lakes to beat the heat. The primary suite is off the living area and includes a sizable custom closet with everything you could need along with a spa-like bathroom to enjoy a relaxing evening before bed. Upstairs are the additional bedrooms which are generously sized for all of your occupants needs including a large bonus room. There's also a second laundry up to for extra convenience! This wonderful home also included a 12 x 30 Boat dock and sling style lift as well as landscape lighting. Energy savings will be yours with LED Lighting, tankless hot water heaters and spray foam insulation. You also have top rated schools and access to all the shopping, dining and entertainment this wonderful neighborhood offers. This beautiful home is completed and ready to move in- so make an appointment today to view this stunning new home and make it yours.

5 Beds ⋅ 4 Baths ⋅ Long Branch Sub SubDv. ⋅ 32751 Zip Code

PRICE IMPROVEMENT!! New Construction with Winter Park Chain of Lakes Access!! You'll be stunned by this gorgeous coastal style home on a private canal that leads to Lake Maitland. This magnificent residence features 5 bedrooms, a bonus room, pool with a relaxing spa and brand new covered boat dock. Your journey begins in the grand two-story foyer featuring elegant lighting choices which are sure to impress. On the left is your study or flex space which can be used as a an additional bedroom as well. As you step into the generous and open grand room to your left is the elegant wine room. The open kitchen is a chef's dream featuring GE Cafe appliances , including a 36" freestanding range as well an Advantium oven and convection wall oven. Elegant slim shaker cabinetry and a large gathering island for entertaining complete this wonderful space. Off the kitchen is a scullery and laundry area with additional dishwasher and refrigerator for preparing grand holiday spreads. The dining room features an additional bar area with beverage refrigeration and overlooks the pool and canal so you can enjoy the views as you share a meal. Summers by the pool will be filled with grilling on the porch as you enjoy the lanai and days on the famed chain of lakes to beat the heat. The primary suite is off the living area and includes a sizable custom closet with everything you could need along with a spa-like bathroom to enjoy a relaxing evening before bed. Upstairs are the additional bedrooms which are generously sized for all of your occupants needs including a large bonus room. There's also a second laundry up to for extra convenience! This wonderful home also included a 12 x 30 Boat dock and sling style lift as well as landscape lighting. Energy savings will be yours with LED Lighting, tankless hot water heaters and spray foam insulation. You also have top rated schools and access to all the shopping, dining and entertainment this wonderful neighborhood offers. This beautiful home is completed and ready to move in- so make an appointment today to view this stunning new home and make it yours.

640 Old Horatio Avenue, Maitland

$235,000

Investor or Rehab Special! Lots of potential with this mid-century gem. Great location on a dead-end street just a short distance to 17/92 and all of the action that Maitland has to offer including the Maitland Farmer's Market, Community Park, Maitland Art Center, Enzian Theater, and the Maitland Art Festival at Lake Lily. Plenty of restaurant and grocery options in close proximity as well as easy access to I-4, Winter Park, and downtown Orlando. Schedule your showing today!

2 Beds ⋅ 2 Baths ⋅ Lake Eulalia Heights SubDv. ⋅ 32751 Zip Code

Investor or Rehab Special! Lots of potential with this mid-century gem. Great location on a dead-end street just a short distance to 17/92 and all of the action that Maitland has to offer including the Maitland Farmer's Market, Community Park, Maitland Art Center, Enzian Theater, and the Maitland Art Festival at Lake Lily. Plenty of restaurant and grocery options in close proximity as well as easy access to I-4, Winter Park, and downtown Orlando. Schedule your showing today!

6 Barnard Court, Maitland

$670,000

Charming Dommerich Estates pool home with many recent updates and great flex space. Beautifully renovated kitchen with granite counters, stainless steel appliances, double ovens, side cabinets with lighted glass uppers, bar seating, and adjacent multi-purpose nook. The kitchen opens to family room with fireplace, and to sunporch with picture windows overlooking the pool. The downstairs houses three bedrooms (including original master bedroom) and two bathrooms. Addition upstairs created a primary suite with full bathroom and walk-in closet. Features include gleaming terrazzo floors and Pella energy-star windows throughout the downstairs, French doors, and a large screened porch. The backyard has a pool, a side brick patio, and pavered walkway. Improvements include AC 2023, electric panel & main breaker panel outside 2023, hot water heater 2023 and replumbed. Four Point Inspection report available. Amazing location, walking distance to Dommerich Elementary and Maitland Middle School, as well as one block to Maitland Community Park boardwalk. Dommerich Estates community lake access on Dommerich Drive.

4 Beds ⋅ 3 Baths ⋅ Dommerich Estates 4th Add SubDv. ⋅ 32751 Zip Code

Charming Dommerich Estates pool home with many recent updates and great flex space. Beautifully renovated kitchen with granite counters, stainless steel appliances, double ovens, side cabinets with lighted glass uppers, bar seating, and adjacent multi-purpose nook. The kitchen opens to family room with fireplace, and to sunporch with picture windows overlooking the pool. The downstairs houses three bedrooms (including original master bedroom) and two bathrooms. Addition upstairs created a primary suite with full bathroom and walk-in closet. Features include gleaming terrazzo floors and Pella energy-star windows throughout the downstairs, French doors, and a large screened porch. The backyard has a pool, a side brick patio, and pavered walkway. Improvements include AC 2023, electric panel & main breaker panel outside 2023, hot water heater 2023 and replumbed. Four Point Inspection report available. Amazing location, walking distance to Dommerich Elementary and Maitland Middle School, as well as one block to Maitland Community Park boardwalk. Dommerich Estates community lake access on Dommerich Drive.

1821 Mohican Trail, Maitland

$999,000

Prepare to fall head over heels for this meticulously reimagined mid-century modern POOL home, located in the highly sought after Dommerich Estates neighborhood. This home features 5 Bedrooms, 3 Bathrooms and is situated on a spacious 1/3 acre lot! The existing 2-Car Carport can easily be converted into a 2-Car Garage for only $5K and the home can be sold almost entirely FURNISHED (please inquire for more information). Recent updates include a New Roof (2020), HVAC System (2021), Pool Resurfaced and New Pool Pump (2023), Hot Water Heater (2018), Kitchen Appliances (2018) and New Underground Power Lines (2025) and Updated PVC Plumbing! From the moment you step inside, you’re welcomed by an open-concept living space with a beautifully updated kitchen that flows directly into the living room. The kitchen features granite countertops and soft close cabinets & drawers with additional storage located on the opposite side of the island. The living room features beautiful espresso tile flooring, exposed wood ceilings, a wood-burning fireplace, and an abundance of natural light. The split floor plan is thoughtfully designed to maximize privacy and comfort with 3 bedrooms one side in addition to the primary suite. The primary suite retreat features his and hers closets and a spa-like en-suite bathroom featuring a freestanding soaking tub, a glass-enclosed shower, and a double sink vanity. On the other side, you'll find a guest bedroom with its own en-suite bathroom offering perfect escape for visitors or extended family. Don't forget to step outside to your own outdoor oasis with a deep, oversized pool, plenty of green space and the perfect set up for ultimate relaxation or unforgettable gatherings. Location? It doesn’t get better! Schools are located within a very short drive or bike ride, you are a 13 min drive to Winter Park's famous Park Ave, 18 min to Downtown Orlando Nestled just minutes from Maitland Park, scenic boardwalks, trails, and nature preserves. Plus, you’re a stone’s throw from Publix and some of the area’s best restaurants, keeping convenience and entertainment at your fingertips. This is more than just a home—it’s a lifestyle. Optional HOA with boat ramp access to Lake Minnehaha with access to the exclusive Winter Park Chain of Lakes. Zoned for top rated schools Dommerich Elementary, Maitland Middle and Winter Park High School!

5 Beds ⋅ 3 Baths ⋅ Dommerich Estates SubDv. ⋅ 32751 Zip Code

Prepare to fall head over heels for this meticulously reimagined mid-century modern POOL home, located in the highly sought after Dommerich Estates neighborhood. This home features 5 Bedrooms, 3 Bathrooms and is situated on a spacious 1/3 acre lot! The existing 2-Car Carport can easily be converted into a 2-Car Garage for only $5K and the home can be sold almost entirely FURNISHED (please inquire for more information). Recent updates include a New Roof (2020), HVAC System (2021), Pool Resurfaced and New Pool Pump (2023), Hot Water Heater (2018), Kitchen Appliances (2018) and New Underground Power Lines (2025) and Updated PVC Plumbing! From the moment you step inside, you’re welcomed by an open-concept living space with a beautifully updated kitchen that flows directly into the living room. The kitchen features granite countertops and soft close cabinets & drawers with additional storage located on the opposite side of the island. The living room features beautiful espresso tile flooring, exposed wood ceilings, a wood-burning fireplace, and an abundance of natural light. The split floor plan is thoughtfully designed to maximize privacy and comfort with 3 bedrooms one side in addition to the primary suite. The primary suite retreat features his and hers closets and a spa-like en-suite bathroom featuring a freestanding soaking tub, a glass-enclosed shower, and a double sink vanity. On the other side, you'll find a guest bedroom with its own en-suite bathroom offering perfect escape for visitors or extended family. Don't forget to step outside to your own outdoor oasis with a deep, oversized pool, plenty of green space and the perfect set up for ultimate relaxation or unforgettable gatherings. Location? It doesn’t get better! Schools are located within a very short drive or bike ride, you are a 13 min drive to Winter Park's famous Park Ave, 18 min to Downtown Orlando Nestled just minutes from Maitland Park, scenic boardwalks, trails, and nature preserves. Plus, you’re a stone’s throw from Publix and some of the area’s best restaurants, keeping convenience and entertainment at your fingertips. This is more than just a home—it’s a lifestyle. Optional HOA with boat ramp access to Lake Minnehaha with access to the exclusive Winter Park Chain of Lakes. Zoned for top rated schools Dommerich Elementary, Maitland Middle and Winter Park High School!

1665 Cheyenne Trail, Maitland

$299,999

One or more photo(s) has been virtually staged. Experience the best of Maitland living in this two-story condo nestled in the gated Lake Faith Villas community. Offering 1,860 square feet of comfortable living space, this home features an enormous open floor plan with updated vinyl flooring on the lower level. The living and dining areas flow seamlessly, opening to a private back patio with lush garden views—perfect for relaxing or entertaining. The updated kitchen includes appliances, an oversized pantry, and an eat-in nook with a sliding glass door that fills the space with natural light. Upstairs and with new carpet, the expansive primary bedroom boasts a walk-in closet and ensuite bathroom. A second bedroom is located on the opposite end of the upstairs living space, offering privacy and versatility. Additional highlights include two private patios, newer roof and AC (both replaced in 2022), and scenic park-like views. The condo association covers water, gate security, pool access, and lawn maintenance—offering a low-maintenance lifestyle. Conveniently located with easy access to I-4, State Road 414, and just 15 minutes from downtown Orlando, this home is close to shopping, dining, and nearby cities like Winter Park and Altamonte Springs. Schedule your exclusive showing today and discover what makes this condo the perfect place to call home!

3 Beds ⋅ 3 Baths ⋅ Lake Faith Villas Condo SubDv. ⋅ 32751 Zip Code

One or more photo(s) has been virtually staged. Experience the best of Maitland living in this two-story condo nestled in the gated Lake Faith Villas community. Offering 1,860 square feet of comfortable living space, this home features an enormous open floor plan with updated vinyl flooring on the lower level. The living and dining areas flow seamlessly, opening to a private back patio with lush garden views—perfect for relaxing or entertaining. The updated kitchen includes appliances, an oversized pantry, and an eat-in nook with a sliding glass door that fills the space with natural light. Upstairs and with new carpet, the expansive primary bedroom boasts a walk-in closet and ensuite bathroom. A second bedroom is located on the opposite end of the upstairs living space, offering privacy and versatility. Additional highlights include two private patios, newer roof and AC (both replaced in 2022), and scenic park-like views. The condo association covers water, gate security, pool access, and lawn maintenance—offering a low-maintenance lifestyle. Conveniently located with easy access to I-4, State Road 414, and just 15 minutes from downtown Orlando, this home is close to shopping, dining, and nearby cities like Winter Park and Altamonte Springs. Schedule your exclusive showing today and discover what makes this condo the perfect place to call home!

311 W Lake Faith Drive, Maitland

$1,000,000

A home of distinction in the quaint cul-de-sac neighborhood of Versailles in Maitland. Tucked away in an area anchored by Lake Minnehaha where sidewalks frame the streets and are canopied by mature trees, this home rests on almost a ½-acre lot. This two-story 3,175-square-foot residence enjoys timeless architecture with four bedrooms, 2.5 baths in the main house and one bedroom and full bath with generous living space in the casita. The guest house offers so many possibilities and adds charm and function unique to this home. The main house welcomes you in through a gracious foyer with a mosaic tile inlay and opens to living and dining spaces where windows were added to invite in natural light. Kitchen is completely renovated with custom built in-set shaker cabinets manufactured in the Tennessee foothills, marble countertops with Kohler farmhouse sink, marble subway tile backsplash, and Thermador gas range stovetop and stacking oven and microwave combo. A peninsula style counter for ease of entertaining and counter dining. Kitchen and family spaces combine with a fireplace focal point flanked by windows, a space for entertaining with doors that lead to covered porch and screened pool. Green space is abundant in the backyard and front where the home wraps the cul-de-sac corner. Artisan millwork features include crown molding, wainscotting throughout the downstairs and guesthouse, custom-built desk and credenza and custom-built cabinets in family room. The primary bedroom upstairs is spacious with French doors opening to second story deck that provides a peaceful retreat and space for alfresco dining. Primary bath includes a double sink vanity, large linen closet and oversized shower. The guest house is an incredible bonus to this special home and underwent complete renovation in 2020 which included a full bath restoration with designer tile selections, updated large soaking tub and vanity with marble countertop, and updated baseboards and wainscotting. Vaulted ceilings add spacious feel and all-weather awnings with metal roof add to the character. Other upgrades to home include new roof and skylights 2024, Hardie board siding with low maintenance and long-term life, upgraded air-conditioning units in main home and guest house, updated pool pump, storage shed, mature landscaping, recessed lighting and an incredibly large lot for the area. Versailles neighborhood is a quaint community with only 65 homes and zoned for great Orange County Schools which include Lake Sybelia, Maitland Middle and Winter Park High Schools and easy travel to nearby private schools. Access to Interstate 4 is close as well as major roadways. A quick visit out the back gate to the Maitland Community Park provides excellent entertainment options including two playgrounds, basketball, racquetball, and six tennis courts and fitness trails. Versailles neighborhood residents have access to Lake Minnehaha through a dedicated lake lot. A paved walking path that leads straight to Publix and many dining options including Pizza Bruno, Foxtail Coffee, Starbucks and more. Lifestyle abounds at this property and a home like this doesn’t come up often. Call today for a private showing.

5 Beds ⋅ 4 Baths ⋅ Versailles SubDv. ⋅ 32751 Zip Code

A home of distinction in the quaint cul-de-sac neighborhood of Versailles in Maitland. Tucked away in an area anchored by Lake Minnehaha where sidewalks frame the streets and are canopied by mature trees, this home rests on almost a ½-acre lot. This two-story 3,175-square-foot residence enjoys timeless architecture with four bedrooms, 2.5 baths in the main house and one bedroom and full bath with generous living space in the casita. The guest house offers so many possibilities and adds charm and function unique to this home. The main house welcomes you in through a gracious foyer with a mosaic tile inlay and opens to living and dining spaces where windows were added to invite in natural light. Kitchen is completely renovated with custom built in-set shaker cabinets manufactured in the Tennessee foothills, marble countertops with Kohler farmhouse sink, marble subway tile backsplash, and Thermador gas range stovetop and stacking oven and microwave combo. A peninsula style counter for ease of entertaining and counter dining. Kitchen and family spaces combine with a fireplace focal point flanked by windows, a space for entertaining with doors that lead to covered porch and screened pool. Green space is abundant in the backyard and front where the home wraps the cul-de-sac corner. Artisan millwork features include crown molding, wainscotting throughout the downstairs and guesthouse, custom-built desk and credenza and custom-built cabinets in family room. The primary bedroom upstairs is spacious with French doors opening to second story deck that provides a peaceful retreat and space for alfresco dining. Primary bath includes a double sink vanity, large linen closet and oversized shower. The guest house is an incredible bonus to this special home and underwent complete renovation in 2020 which included a full bath restoration with designer tile selections, updated large soaking tub and vanity with marble countertop, and updated baseboards and wainscotting. Vaulted ceilings add spacious feel and all-weather awnings with metal roof add to the character. Other upgrades to home include new roof and skylights 2024, Hardie board siding with low maintenance and long-term life, upgraded air-conditioning units in main home and guest house, updated pool pump, storage shed, mature landscaping, recessed lighting and an incredibly large lot for the area. Versailles neighborhood is a quaint community with only 65 homes and zoned for great Orange County Schools which include Lake Sybelia, Maitland Middle and Winter Park High Schools and easy travel to nearby private schools. Access to Interstate 4 is close as well as major roadways. A quick visit out the back gate to the Maitland Community Park provides excellent entertainment options including two playgrounds, basketball, racquetball, and six tennis courts and fitness trails. Versailles neighborhood residents have access to Lake Minnehaha through a dedicated lake lot. A paved walking path that leads straight to Publix and many dining options including Pizza Bruno, Foxtail Coffee, Starbucks and more. Lifestyle abounds at this property and a home like this doesn’t come up often. Call today for a private showing.

1002 Versailles Court, Maitland

$465,000

Luxury Corner Unit with Stunning Lake Views – Fully Remodeled Experience breathtaking lake views from this fully remodeled, 2-bedroom, 2-bathroom luxury corner unit in the heart of Maitland. With 1,248 sq. ft. of beautifully designed space, this home is flooded with natural light from multiple exposures, setting it apart from other units in the building. Property Features: - Exclusive Corner Unit: Enjoy more privacy and an abundance of natural light from extra windows. - Complete Luxury Renovation: Every detail has been upgraded with high-end materials, from designer flooring to custom cabinetry and quartz countertops. - Stunning Lake Views: Take in expansive waterfront views from your private balcony and living room. - Spacious Open Layout: Floor-to-ceiling windows create an airy, inviting atmosphere with tons of natural light. - Gourmet Kitchen: Features top-of-the-line stainless steel appliances, a stylish backsplash, and a modern waterfall island, perfect for entertaining. - Spa-Inspired Bathrooms: High-end vanities, marble finishes, and a glass-enclosed rain shower create a retreat-like feel. - Large Primary Closet: The primary bedroom features a spacious closet, providing ample storage without compromising space. - Peaceful Retreat: While the primary bedroom does not have a lake view, it offers a quiet and private atmosphere for ultimate relaxation. Thriving Community & Growing Investment Potential: - Booming Development: Maitland is experiencing rapid growth with new construction, shopping centers, and supermarkets, making it an ideal place to invest. - Increasing Property Values: As the area continues to develop, property values are steadily rising, offering a great long-term investment opportunity. - Resort-Style Amenities: Enjoy access to a pool, fitness center, clubhouse, and beautifully maintained landscaping. - Prime Location: Just minutes from Park Avenue in Winter Park, offering world-class dining, shopping, and entertainment. - Top-Rated Schools: Zoned for Dommerich Elementary (9/10) and Winter Park High (7/10). Convenient & Connected: Close to major highways, downtown Orlando, and Orlando International Airport. **Updates & Maintenance:** - Brand-New Water Heater and newer AC in the unit. - The roof of the community has just been replaced, and the entire building has been fully painted, adding to the appeal of this well-maintained property. This rare corner unit offers unmatched lakefront views, natural light, and is located in a high-growth area with rising value. Schedule your private showing today!

2 Beds ⋅ 2 Baths ⋅ West Cove SubDv. ⋅ 32751 Zip Code

Luxury Corner Unit with Stunning Lake Views – Fully Remodeled Experience breathtaking lake views from this fully remodeled, 2-bedroom, 2-bathroom luxury corner unit in the heart of Maitland. With 1,248 sq. ft. of beautifully designed space, this home is flooded with natural light from multiple exposures, setting it apart from other units in the building. Property Features: - Exclusive Corner Unit: Enjoy more privacy and an abundance of natural light from extra windows. - Complete Luxury Renovation: Every detail has been upgraded with high-end materials, from designer flooring to custom cabinetry and quartz countertops. - Stunning Lake Views: Take in expansive waterfront views from your private balcony and living room. - Spacious Open Layout: Floor-to-ceiling windows create an airy, inviting atmosphere with tons of natural light. - Gourmet Kitchen: Features top-of-the-line stainless steel appliances, a stylish backsplash, and a modern waterfall island, perfect for entertaining. - Spa-Inspired Bathrooms: High-end vanities, marble finishes, and a glass-enclosed rain shower create a retreat-like feel. - Large Primary Closet: The primary bedroom features a spacious closet, providing ample storage without compromising space. - Peaceful Retreat: While the primary bedroom does not have a lake view, it offers a quiet and private atmosphere for ultimate relaxation. Thriving Community & Growing Investment Potential: - Booming Development: Maitland is experiencing rapid growth with new construction, shopping centers, and supermarkets, making it an ideal place to invest. - Increasing Property Values: As the area continues to develop, property values are steadily rising, offering a great long-term investment opportunity. - Resort-Style Amenities: Enjoy access to a pool, fitness center, clubhouse, and beautifully maintained landscaping. - Prime Location: Just minutes from Park Avenue in Winter Park, offering world-class dining, shopping, and entertainment. - Top-Rated Schools: Zoned for Dommerich Elementary (9/10) and Winter Park High (7/10). Convenient & Connected: Close to major highways, downtown Orlando, and Orlando International Airport. **Updates & Maintenance:** - Brand-New Water Heater and newer AC in the unit. - The roof of the community has just been replaced, and the entire building has been fully painted, adding to the appeal of this well-maintained property. This rare corner unit offers unmatched lakefront views, natural light, and is located in a high-growth area with rising value. Schedule your private showing today!

1100 S Orlando Avenue Unit 301, Maitland

$1,000,000

Reduced $200K to help with remodeling if desired!! One owner custom built modern contemporary nestled in a secluded area in The Oaks of Maitland! Spacious home offers a soaring vaulted cedar beamed ceiling in family room with wet bar and floor to ceiling wood burning stone fireplace. Located on a cul-de-sac lot with a circular paved driveway and oversized side entry garage, the backyard includes a putting green and creek running 170ft. along back boundary. 1/2 acre + lot includes azaleas, camelias, lilies, hibiscus, staghorn ferns, copper plants, magnolia tree, tabebuia trees, fig tree, etc. Deeded access to the Winter Park chain of lakes thru the neighborhood HOA boat ramp with access to Lake Minnehaha available with a yearly fee. Walking distance to Maitland Community Park with playground, exercise paths, tennis courts, picnic grounds and more! New roof and newer front double hung insulated windows! Cherry kitchen cabinets, granite countertops, sink hot water dispenser and beautiful 8 panel interior wood doors throughout home! The entire 2nd floor is a primary suite including a large walk-thru closet, bathroom, and den/study/exercise room! Three bedrooms on first floor with one that could be a primary bedroom if steps cause a problem. Two other 1st floor bedrooms share a tub-shower with each having their own toilet and vanity.

4 Beds ⋅ 4 Baths ⋅ Oaks Maitland SubDv. ⋅ 32751 Zip Code

Reduced $200K to help with remodeling if desired!! One owner custom built modern contemporary nestled in a secluded area in The Oaks of Maitland! Spacious home offers a soaring vaulted cedar beamed ceiling in family room with wet bar and floor to ceiling wood burning stone fireplace. Located on a cul-de-sac lot with a circular paved driveway and oversized side entry garage, the backyard includes a putting green and creek running 170ft. along back boundary. 1/2 acre + lot includes azaleas, camelias, lilies, hibiscus, staghorn ferns, copper plants, magnolia tree, tabebuia trees, fig tree, etc. Deeded access to the Winter Park chain of lakes thru the neighborhood HOA boat ramp with access to Lake Minnehaha available with a yearly fee. Walking distance to Maitland Community Park with playground, exercise paths, tennis courts, picnic grounds and more! New roof and newer front double hung insulated windows! Cherry kitchen cabinets, granite countertops, sink hot water dispenser and beautiful 8 panel interior wood doors throughout home! The entire 2nd floor is a primary suite including a large walk-thru closet, bathroom, and den/study/exercise room! Three bedrooms on first floor with one that could be a primary bedroom if steps cause a problem. Two other 1st floor bedrooms share a tub-shower with each having their own toilet and vanity.

1606 The Oaks Drive, Maitland

$2,150,000

This stunning contemporary lakefront residence, completed in 2019, offers almost 6,000 square feet of refined living space with magnificent elevated views of Lake Catherine. Thoughtfully designed with elegant finishes, this two-story, five-bedroom, 5.5-bath residence, plus office/media room and open flex/lounge area that showcases a bright/open floor plan enjoying expansive walls of glass windows/doors that frame the serene waterfront setting. The main level features sleek porcelain tile flooring, soaring ceilings, and sun-drenched interiors. Two separate back-to-back fireplaces connect the formal dining area and living room, while the spacious family room is bathed in natural light. The modern kitchen boasts a large island, high-end appliances, a hidden pantry and laundry room, and a built-in coffee maker. The first-floor primary suite offers lake views, a custom walk-in closet and a spa-like bath with dual sinks, a walk-in shower and a jetted soaking tub. A versatile flex space adjacent to the suite is ideal for a fitness area, office or private retreat. A floating staircase leads to the second level, where a generous bonus room/game room, two additional bedroom suites with walk-in closets and en-suite baths, and another flex room await. The expansive second-floor balcony overlooks the sleek glass-railed pool and provides uninterrupted lake views. A separate parcel across the street includes a private covered dock on the 21-acre Lake Catherine, ideal for kayaking and paddleboarding. The two-car garage, accessed through a gated rear entry, adds convenience and security. In a tranquil, private setting, yet minutes from Maitland’s cultural corridor as well as the vibrant shopping and dining of Park Avenue, this exceptional property seamlessly blends contemporary luxury with lakeside tranquility.

5 Beds ⋅ 6 Baths ⋅ Sheridan Place SubDv. ⋅ 32751 Zip Code

This stunning contemporary lakefront residence, completed in 2019, offers almost 6,000 square feet of refined living space with magnificent elevated views of Lake Catherine. Thoughtfully designed with elegant finishes, this two-story, five-bedroom, 5.5-bath residence, plus office/media room and open flex/lounge area that showcases a bright/open floor plan enjoying expansive walls of glass windows/doors that frame the serene waterfront setting. The main level features sleek porcelain tile flooring, soaring ceilings, and sun-drenched interiors. Two separate back-to-back fireplaces connect the formal dining area and living room, while the spacious family room is bathed in natural light. The modern kitchen boasts a large island, high-end appliances, a hidden pantry and laundry room, and a built-in coffee maker. The first-floor primary suite offers lake views, a custom walk-in closet and a spa-like bath with dual sinks, a walk-in shower and a jetted soaking tub. A versatile flex space adjacent to the suite is ideal for a fitness area, office or private retreat. A floating staircase leads to the second level, where a generous bonus room/game room, two additional bedroom suites with walk-in closets and en-suite baths, and another flex room await. The expansive second-floor balcony overlooks the sleek glass-railed pool and provides uninterrupted lake views. A separate parcel across the street includes a private covered dock on the 21-acre Lake Catherine, ideal for kayaking and paddleboarding. The two-car garage, accessed through a gated rear entry, adds convenience and security. In a tranquil, private setting, yet minutes from Maitland’s cultural corridor as well as the vibrant shopping and dining of Park Avenue, this exceptional property seamlessly blends contemporary luxury with lakeside tranquility.

641 Lake Catherine Drive, Maitland

$210,000

SELLER MOTIVATED, REDUCED! Rare opportunity for spacious condo with beautiful lake, pool and open space view condo in the desirable Park Lake community of Maitland. Close to major transportation routes, employment centers, Park Avenue/Winter Park, Alt. Spgs. and downtown Orlando. Freshly painted. 3/3 with TWO PRIMARY SUITES on 2nd floor with EN-SUITE bathrooms, one of which has a walk-in whirlpool tub and private balcony overlooking greenspace, pool and lake. Downstairs bedroom with adjacent full bath can also be used as den, office or mother-in-law bedroom and has sliding glass door to private courtyard. Great for any generation(s). Many recent bath and kitchen upgrades as well as relatively recent AC, water heater and dishwasher. All rooms have ceiling fans and all bathrooms have exhaust fans. Freshly painted. New circuit breaker panels. Recent re-roof, paint and fences by Condo Association. SEE FLOOR PLAN FOR LAYOUT AND DIMENSIONS (No warranties as to accuracy- confirm for Buyer) MUST SEE !!!

3 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo SubDv. ⋅ 32751 Zip Code

SELLER MOTIVATED, REDUCED! Rare opportunity for spacious condo with beautiful lake, pool and open space view condo in the desirable Park Lake community of Maitland. Close to major transportation routes, employment centers, Park Avenue/Winter Park, Alt. Spgs. and downtown Orlando. Freshly painted. 3/3 with TWO PRIMARY SUITES on 2nd floor with EN-SUITE bathrooms, one of which has a walk-in whirlpool tub and private balcony overlooking greenspace, pool and lake. Downstairs bedroom with adjacent full bath can also be used as den, office or mother-in-law bedroom and has sliding glass door to private courtyard. Great for any generation(s). Many recent bath and kitchen upgrades as well as relatively recent AC, water heater and dishwasher. All rooms have ceiling fans and all bathrooms have exhaust fans. Freshly painted. New circuit breaker panels. Recent re-roof, paint and fences by Condo Association. SEE FLOOR PLAN FOR LAYOUT AND DIMENSIONS (No warranties as to accuracy- confirm for Buyer) MUST SEE !!!

607 Waverly Lane Unit 403, Maitland

$1,920,000

Lake Sybelia is calling. This gracious home is on a private spring-fed skiable lake and tucked away on a tree-lined brick street, offering a lifestyle that is unparalleled. On about three quarters of an acre and almost 120 feet of linear lake frontage, it is a wide view of this pristine waterway. A covered boat dock is updated with an electronic lift and new cradle cabling. An open deck with all-weather planks runs along the waterfront and sandy shore to capture all the lake offers. Abundant lakeside green space makes entertaining simple. This one-story home features five bedrooms and four baths with an additional guest house and has been completely reimagined while keeping the charm of vintage Maitland. The main house includes a split four-bedroom plan for privacy with open living spaces that seamlessly blend into one another. Gorgeous warm European white oak wood floors that ground the spaces and walls are crisp and clean with level five drywall finish. Handcrafted European white oak custom built-ins in dining and living spaces add to the style of this comfortable California-inspired ranch. Dining room custom bar adds function and flair with reflecting mirror back that elegantly finishes this appointment. Tumbled limestone floors in the kitchen, front entry and dining area are neutral toned and add character to the timeless finishes. Custom kitchen is renovated with 42-inch cabinetry, Bosch appliances, Rohl faucets, RH hardware, two porcelain farmhouse sinks with European white oak center island all adorned with imported Dolomite counters and backsplash. The kitchen window above the farmhouse sink brings in the lush greenery of the back courtyard. Loads of storage in the utility, pantry and laundry combination, finished with imported handmade Italian tiles, all designed to make daily functions a breeze and beautiful! An independent guest house completes the home with vaulted ceilings with wood beams, original wood floors, spacious living, efficiency kitchen, full bath and bedroom nook. This multi-functional space is versatile and includes an office area but certainly can be used for what fits your lifestyle. Other enhancements include fully renovated baths consistent with the elevated finishes and selections of overall home, and features European white oak built-in cabinets, imported Spanish and Moroccan tile, in common with architectural lighting. Also, all trim, doors, hardware and moldings were replaced, new roofs on all three structures in 2025, RH linen drapes in living and primary, serviced and operational fireplaces and fresh landscaping. Every detail is accounted for and in pristine location. Visit downtown Maitland, enjoy Lake Lily, community events and weekly farmers market, award-winning restaurants and great community parks. Don’t miss the opportunity of a lifetime to own a lakefront in Florida which continues to be a growing investment.

5 Beds ⋅ 4 Baths ⋅ Maitland Club SubDv. ⋅ 32751 Zip Code

Lake Sybelia is calling. This gracious home is on a private spring-fed skiable lake and tucked away on a tree-lined brick street, offering a lifestyle that is unparalleled. On about three quarters of an acre and almost 120 feet of linear lake frontage, it is a wide view of this pristine waterway. A covered boat dock is updated with an electronic lift and new cradle cabling. An open deck with all-weather planks runs along the waterfront and sandy shore to capture all the lake offers. Abundant lakeside green space makes entertaining simple. This one-story home features five bedrooms and four baths with an additional guest house and has been completely reimagined while keeping the charm of vintage Maitland. The main house includes a split four-bedroom plan for privacy with open living spaces that seamlessly blend into one another. Gorgeous warm European white oak wood floors that ground the spaces and walls are crisp and clean with level five drywall finish. Handcrafted European white oak custom built-ins in dining and living spaces add to the style of this comfortable California-inspired ranch. Dining room custom bar adds function and flair with reflecting mirror back that elegantly finishes this appointment. Tumbled limestone floors in the kitchen, front entry and dining area are neutral toned and add character to the timeless finishes. Custom kitchen is renovated with 42-inch cabinetry, Bosch appliances, Rohl faucets, RH hardware, two porcelain farmhouse sinks with European white oak center island all adorned with imported Dolomite counters and backsplash. The kitchen window above the farmhouse sink brings in the lush greenery of the back courtyard. Loads of storage in the utility, pantry and laundry combination, finished with imported handmade Italian tiles, all designed to make daily functions a breeze and beautiful! An independent guest house completes the home with vaulted ceilings with wood beams, original wood floors, spacious living, efficiency kitchen, full bath and bedroom nook. This multi-functional space is versatile and includes an office area but certainly can be used for what fits your lifestyle. Other enhancements include fully renovated baths consistent with the elevated finishes and selections of overall home, and features European white oak built-in cabinets, imported Spanish and Moroccan tile, in common with architectural lighting. Also, all trim, doors, hardware and moldings were replaced, new roofs on all three structures in 2025, RH linen drapes in living and primary, serviced and operational fireplaces and fresh landscaping. Every detail is accounted for and in pristine location. Visit downtown Maitland, enjoy Lake Lily, community events and weekly farmers market, award-winning restaurants and great community parks. Don’t miss the opportunity of a lifetime to own a lakefront in Florida which continues to be a growing investment.

1100 S Lake Sybelia Drive, Maitland

$2,800,000

Once-in-a-lifetime opportunity to own over 1.5 acres with .5 acre high and dry with approximately 110 ft waterfront on the Whitecaps Circle peninsula on the north shore of Lake Maitland! The property has southern exposure enjoying sunrise, sunsets and view of Dog Island. The lot includes front entrance gate, east side masonry wall, seawall, boathouse and dock, and all are all sold as-is. Adjacent property on 127 Whitecaps Circle is also for sale. Purchasing both properties would give the new owner a very unique and stunning peninsula on Lake Maitland on the famed Winter Park Chain of Lakes! Having water frontage on three sides provides complete panoramic views. The new owner could renovate the current home or build their dream home! See MLS# O620214

Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

Once-in-a-lifetime opportunity to own over 1.5 acres with .5 acre high and dry with approximately 110 ft waterfront on the Whitecaps Circle peninsula on the north shore of Lake Maitland! The property has southern exposure enjoying sunrise, sunsets and view of Dog Island. The lot includes front entrance gate, east side masonry wall, seawall, boathouse and dock, and all are all sold as-is. Adjacent property on 127 Whitecaps Circle is also for sale. Purchasing both properties would give the new owner a very unique and stunning peninsula on Lake Maitland on the famed Winter Park Chain of Lakes! Having water frontage on three sides provides complete panoramic views. The new owner could renovate the current home or build their dream home! See MLS# O620214

125 Whitecaps Circle, Maitland

$3,200,000

One of a kind and once in a lifetime opportunity! A stunning lakefront peninsula with panoramic views off the north shore of Lake Maitland, the largest lake on the famed Winter Park Chain of Lakes, is now available. The estate is surrounded on 2 sides with approximately 300ft of lake frontage, 1.54 acres total and .7 acre dry. The home was designed by Nils Schweizer, a student and representative of Frank Lloyd Wright in Central Florida. Was later renovated adding a pitched roof and screened lanai with a pool/spa overlooking the lake! The 4 bedroom, 2.5 bath and 3 car-garage home with workshop has an abundance of windows and viewing areas to capture the beauty of central Florida lakes. This unmatched property has sunrise and sunset views looking out to Dog Island, Summerland Avenue tip, and the Isle of Sicily. The paver-drive and walkway lined with crepe myrtles, plumeria trees and hanging stag horn ferns welcome guests to the covered front porch and the dramatic foyer. Steps lead to the upper living room with wood floors, fireplace and 3 walls of glass and a balcony for breathtaking views of Lake Maitland. Nearby is an office with built-ins, ceiling fans and French doors opening to the immaculate landscape. The east wing leads to the primary bedroom having gorgeous views of sunsets, built-ins, fireplace and spacious contemporary bath: oversized walk-in shower, whirlpool tub, dual vanities and closets. Nearby is the dining room and custom kitchen. The dining room has built-ins and glass sliders to covered pool lanai - perfect for al fresco dining with pool and lake views. The kitchen has designer cabinets, granite counters, butcher block island and pass-through window to the pool wet bar. The kitchen sitting bar opens to the family room with wood floors, a breakfast nook and sliders to the screened pool lanai with 270 degree views of water! The north wing has 3 additional bedrooms and a full bath. The bonus room with vaulted ceilings, fans and glass sliders is ideal for a personal gym, theatre, or large den: it opens to either the 3-car garage or paver walkway to the workshop and backyard. A year-round personal resort with noteworthy plants for the gardener, dedicated workshop, hot tub and large pool overlooking the lake The partially enclosed boat house with a sitting deck is a special spot to enjoy sunrises and sunsets! Home’s generator and 250 gallon propane tank assure you of power! Renovate the current home or start fresh to build your dream home! This property is being sold as-is. The adjacent cleared lot on 125 Whitecaps Circle is also for sale. Purchasing both properties would give the new owner a very unique and stunning peninsula parcel on Lake Maitland on the famed Winter Park Chain of Lakes! See MLS#O6279215

4 Beds ⋅ 3 Baths ⋅ Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

One of a kind and once in a lifetime opportunity! A stunning lakefront peninsula with panoramic views off the north shore of Lake Maitland, the largest lake on the famed Winter Park Chain of Lakes, is now available. The estate is surrounded on 2 sides with approximately 300ft of lake frontage, 1.54 acres total and .7 acre dry. The home was designed by Nils Schweizer, a student and representative of Frank Lloyd Wright in Central Florida. Was later renovated adding a pitched roof and screened lanai with a pool/spa overlooking the lake! The 4 bedroom, 2.5 bath and 3 car-garage home with workshop has an abundance of windows and viewing areas to capture the beauty of central Florida lakes. This unmatched property has sunrise and sunset views looking out to Dog Island, Summerland Avenue tip, and the Isle of Sicily. The paver-drive and walkway lined with crepe myrtles, plumeria trees and hanging stag horn ferns welcome guests to the covered front porch and the dramatic foyer. Steps lead to the upper living room with wood floors, fireplace and 3 walls of glass and a balcony for breathtaking views of Lake Maitland. Nearby is an office with built-ins, ceiling fans and French doors opening to the immaculate landscape. The east wing leads to the primary bedroom having gorgeous views of sunsets, built-ins, fireplace and spacious contemporary bath: oversized walk-in shower, whirlpool tub, dual vanities and closets. Nearby is the dining room and custom kitchen. The dining room has built-ins and glass sliders to covered pool lanai - perfect for al fresco dining with pool and lake views. The kitchen has designer cabinets, granite counters, butcher block island and pass-through window to the pool wet bar. The kitchen sitting bar opens to the family room with wood floors, a breakfast nook and sliders to the screened pool lanai with 270 degree views of water! The north wing has 3 additional bedrooms and a full bath. The bonus room with vaulted ceilings, fans and glass sliders is ideal for a personal gym, theatre, or large den: it opens to either the 3-car garage or paver walkway to the workshop and backyard. A year-round personal resort with noteworthy plants for the gardener, dedicated workshop, hot tub and large pool overlooking the lake The partially enclosed boat house with a sitting deck is a special spot to enjoy sunrises and sunsets! Home’s generator and 250 gallon propane tank assure you of power! Renovate the current home or start fresh to build your dream home! This property is being sold as-is. The adjacent cleared lot on 125 Whitecaps Circle is also for sale. Purchasing both properties would give the new owner a very unique and stunning peninsula parcel on Lake Maitland on the famed Winter Park Chain of Lakes! See MLS#O6279215

127 Whitecaps Circle, Maitland

$412,500

Welcome to The Moorings. This 4th-floor condo in the rarely available Moorings community is located directly across from Lake Lily. This spacious 2-bedroom, 2-bathroom unit offers breathtaking views of Lake Maitland from the living room and screened-in balcony. Step inside to discover a bright and airy living area with updated flooring, perfect for entertaining or relaxing. The kitchen and bathrooms retain their original 1980's charm, offering a unique opportunity for customization. The primary suite features a walk-in closet and an en-suite bathroom with a tub and separate shower. Enjoy the convenience of an in-unit laundry room with a washer and dryer. The building is equipped with an elevator and stairs for easy access. The Moorings offers fantastic amenities, including a sparkling community pool, boat docks, a pier with a sitting area. fitness center, and clubhouse. Conveniently located near shopping, dining, and entertainment options, this condo is perfect for those seeking a vibrant lifestyle with easy access to all that Maitland and Winter Park has to offer. This condo is available immediately.

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code

Welcome to The Moorings. This 4th-floor condo in the rarely available Moorings community is located directly across from Lake Lily. This spacious 2-bedroom, 2-bathroom unit offers breathtaking views of Lake Maitland from the living room and screened-in balcony. Step inside to discover a bright and airy living area with updated flooring, perfect for entertaining or relaxing. The kitchen and bathrooms retain their original 1980's charm, offering a unique opportunity for customization. The primary suite features a walk-in closet and an en-suite bathroom with a tub and separate shower. Enjoy the convenience of an in-unit laundry room with a washer and dryer. The building is equipped with an elevator and stairs for easy access. The Moorings offers fantastic amenities, including a sparkling community pool, boat docks, a pier with a sitting area. fitness center, and clubhouse. Conveniently located near shopping, dining, and entertainment options, this condo is perfect for those seeking a vibrant lifestyle with easy access to all that Maitland and Winter Park has to offer. This condo is available immediately.

206 Quayside Circle Unit 404, Maitland

$902,000

Location, charm, and timeless style define this stunning 3-bedroom, 3-bath home in the highly sought-after Dommerich Estates of Maitland. Situated on an expansive corner lot and cul de-sac, this beautiful residence offers an exceptional blend of modern luxury and classic character. Step inside to rich wood floors, crown molding, and plantation shutters adorning every window. The spacious family room features a wood-burning fireplace, custom built-in bookshelves, and is wired for surround sound—perfect for cozy nights or entertaining guests. A sunroom/reading nook offers a bright and serene retreat and a bar area that seamlessly flows into the living space. The kitchen boasts granite countertops, and newly upgraded LG & Frigidaire Gallery stainless steel appliances (2023). French doors lead to your private backyard oasis, where a newly renovated pool and paved patio provide a perfect setting for outdoor entertaining. The expansive master suite offers a large walk-in closet and a sunken spa-inspired bath, ensuring a perfect escape at the end of the day. Additional recent upgrades include fresh interior and exterior paint. Newer windows, HVAC 2017 with 10-year warranty, updated plumbing lines, electrical panel updated 2023, and roof was installed 2010, making this home move-in ready. Outside, you'll find a front circular driveway with new pavers for added curb appeal and convenience, plus a rear cul-de-sac location that enhances privacy, accessibility, and outdoor fun for families. The location is unparalleled, close to shopping, restaurants, parks and major roadways. Located just 0.6 miles from Dommerich Elementary, this Dommerich Estates home is also zoned for Winter Park High School. Neighborhood amenities include lake access to Lake Minnehaha. Enjoy nearby attractions/ restaurants, Maitland Community Park, Minnehaha Park and downtown Maitland. This is more than just a home; it’s a lifestyle. Don't miss your chance to own in one of Maitland’s most coveted communities! Schedule your private tour today. *Info recorded in the MLS is intended to be accurate, but NOT GUARANTEED. Home square footage, room sizes and lot size should be independently verified. *

3 Beds ⋅ 3 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code

Location, charm, and timeless style define this stunning 3-bedroom, 3-bath home in the highly sought-after Dommerich Estates of Maitland. Situated on an expansive corner lot and cul de-sac, this beautiful residence offers an exceptional blend of modern luxury and classic character. Step inside to rich wood floors, crown molding, and plantation shutters adorning every window. The spacious family room features a wood-burning fireplace, custom built-in bookshelves, and is wired for surround sound—perfect for cozy nights or entertaining guests. A sunroom/reading nook offers a bright and serene retreat and a bar area that seamlessly flows into the living space. The kitchen boasts granite countertops, and newly upgraded LG & Frigidaire Gallery stainless steel appliances (2023). French doors lead to your private backyard oasis, where a newly renovated pool and paved patio provide a perfect setting for outdoor entertaining. The expansive master suite offers a large walk-in closet and a sunken spa-inspired bath, ensuring a perfect escape at the end of the day. Additional recent upgrades include fresh interior and exterior paint. Newer windows, HVAC 2017 with 10-year warranty, updated plumbing lines, electrical panel updated 2023, and roof was installed 2010, making this home move-in ready. Outside, you'll find a front circular driveway with new pavers for added curb appeal and convenience, plus a rear cul-de-sac location that enhances privacy, accessibility, and outdoor fun for families. The location is unparalleled, close to shopping, restaurants, parks and major roadways. Located just 0.6 miles from Dommerich Elementary, this Dommerich Estates home is also zoned for Winter Park High School. Neighborhood amenities include lake access to Lake Minnehaha. Enjoy nearby attractions/ restaurants, Maitland Community Park, Minnehaha Park and downtown Maitland. This is more than just a home; it’s a lifestyle. Don't miss your chance to own in one of Maitland’s most coveted communities! Schedule your private tour today. *Info recorded in the MLS is intended to be accurate, but NOT GUARANTEED. Home square footage, room sizes and lot size should be independently verified. *

1591 Chippewa Trail, Maitland

$407,000

LAKEFRONT 3-BED / 2-BATH / 2-CAR GARAGE Condo in GATED COMMUNITY of SUNBAY CLUB! This condominium is by far the finest in the entire Sun Bay Community and feels/functions more like a townhouse: SINGLE-STORY / END-UNIT FLOORPLAN with volume ceilings and only one attached neighbor! The home’s layout offers PRISTINE VIEWS of LAKE DESTINY, a private 29-acre lake, from the living areas, owner’s suite and screen/covered porch. HOME HAS BEEN FULLY-RENOVATED with the finest choices possible. THE KITCHEN: Re-envisioned as a smart open-plan remodel with a large center island, built-in pantry, recessed refrigerator & microwave and a coffee-bar / butler’s station with cushioned seating/bench storage. TIMELESS & BEAUTIFUL LEVEL-II GRANITE exceeds your highest expectation. Upgraded cabinetry, shiplap detailing, crown molding, stainless steel apron sink, modern hardware and matching slate-finish LG appliance package. ENTIRE DWELLING: Neutral & modern laminate flooring reaches every corner of the home (no "transition strips” between rooms!). Every window includes remote-operated SOMFY SMART SHADE window coverings throughout the entire home, controlled with the touch of a button! Stone accent walls in the living & dining areas create a perfectly intimate mood, day or night. Vaulted ceilings with 7 skylights fill the home with beautiful daylight (NEW-2024). Corner set fireplace with stone and shiplap detailing. Large owner’s suite connects to screened & covered patio all with peaceful LAKE VIEWS. Extensive renovations continue in the owner’s bath, guest bath, dedicated laundry area, and brick paved entry walk. HIGH-END UPGRADES INCLUDE: lighting, ceiling fans, door hardware, 5¼” baseboards, outlets & rocker panel switches all which make this modern & immaculate home your MOVE-IN READY choice. SUNBAY CLUB: This small enclave of 68 condominiums offers a uniquely private living experience. Behind the iconic blue gates, you will find a beautiful community enhanced with fountains, open grassy areas, a tennis court, lakefront swimming pool and a boat launch perfect for your paddleboard. Sunbay Club replaced all tile roofs, gutters/downspouts, skylights in 2024. Monthly condo fee includes CABLE & HIGH-SPEED INTERNET (Spectrum). Fee also covers: Exterior Maintenance (building/roof), Common-Area/Gate, Landscaping/Irrigation, Lighting/Ponds Maintenance, Pool/Clubhouse Upkeep. Combined, these community services reduce your ownership costs tremendously!! LOCATION: Access within minutes Worldclass “RDV Sportsplex” (Genesis HealthClub), Interstate-4 (Express), Publix, shopping & dining options. Downtown Maitland, Winter Park and Orlando are only a minutes away. Come see why this is the address you will want to call YOUR NEXT HOME!

3 Beds ⋅ 2 Baths ⋅ Sun Bay Club SubDv. ⋅ 32751 Zip Code

LAKEFRONT 3-BED / 2-BATH / 2-CAR GARAGE Condo in GATED COMMUNITY of SUNBAY CLUB! This condominium is by far the finest in the entire Sun Bay Community and feels/functions more like a townhouse: SINGLE-STORY / END-UNIT FLOORPLAN with volume ceilings and only one attached neighbor! The home’s layout offers PRISTINE VIEWS of LAKE DESTINY, a private 29-acre lake, from the living areas, owner’s suite and screen/covered porch. HOME HAS BEEN FULLY-RENOVATED with the finest choices possible. THE KITCHEN: Re-envisioned as a smart open-plan remodel with a large center island, built-in pantry, recessed refrigerator & microwave and a coffee-bar / butler’s station with cushioned seating/bench storage. TIMELESS & BEAUTIFUL LEVEL-II GRANITE exceeds your highest expectation. Upgraded cabinetry, shiplap detailing, crown molding, stainless steel apron sink, modern hardware and matching slate-finish LG appliance package. ENTIRE DWELLING: Neutral & modern laminate flooring reaches every corner of the home (no "transition strips” between rooms!). Every window includes remote-operated SOMFY SMART SHADE window coverings throughout the entire home, controlled with the touch of a button! Stone accent walls in the living & dining areas create a perfectly intimate mood, day or night. Vaulted ceilings with 7 skylights fill the home with beautiful daylight (NEW-2024). Corner set fireplace with stone and shiplap detailing. Large owner’s suite connects to screened & covered patio all with peaceful LAKE VIEWS. Extensive renovations continue in the owner’s bath, guest bath, dedicated laundry area, and brick paved entry walk. HIGH-END UPGRADES INCLUDE: lighting, ceiling fans, door hardware, 5¼” baseboards, outlets & rocker panel switches all which make this modern & immaculate home your MOVE-IN READY choice. SUNBAY CLUB: This small enclave of 68 condominiums offers a uniquely private living experience. Behind the iconic blue gates, you will find a beautiful community enhanced with fountains, open grassy areas, a tennis court, lakefront swimming pool and a boat launch perfect for your paddleboard. Sunbay Club replaced all tile roofs, gutters/downspouts, skylights in 2024. Monthly condo fee includes CABLE & HIGH-SPEED INTERNET (Spectrum). Fee also covers: Exterior Maintenance (building/roof), Common-Area/Gate, Landscaping/Irrigation, Lighting/Ponds Maintenance, Pool/Clubhouse Upkeep. Combined, these community services reduce your ownership costs tremendously!! LOCATION: Access within minutes Worldclass “RDV Sportsplex” (Genesis HealthClub), Interstate-4 (Express), Publix, shopping & dining options. Downtown Maitland, Winter Park and Orlando are only a minutes away. Come see why this is the address you will want to call YOUR NEXT HOME!

1000 Winderley Place Unit 152, Maitland

$305,000

NEWLY ‘ACTIVE’. . . . RENEWED AND REFRESHED . . . AND BACK ON THE MARKET WITH EXCITING NEW UPDATES! NEWLY PAINTED INTERIOR, NEWLY UPDATED MASTER BATH, AND FRESH FRONT AND REAR EXTERIOR UPDATING! If you thought all condos were pretty much the same boring 4 walls, THINK AGAIN! This secluded little jewel is UNIQUE and CONTEMPORARY with TONS OF CHARACTER, and VERY AFFORDABLE! Grab your morning coffee and walk the few steps from your kitchen/patio down TO THE LAKE and soak up a few peaceful moments before starting the rush of your day! This amazing 3 BEDROOM, 2 BATH, OPEN FLOOR PLAN offers 2 MASTER SUITES, plus a 3rd bedroom that could easily be used as an office, den, or playroom. A wood-burning FIREPLACE is at the center of the main living area. The LARGE KITCHEN has plenty of room for an eat-in table. EVERY BEDROOM HAS A SLIDING GLASS DOOR to the outside patio, with beautiful OVER-SIZED WINDOWS, letting in tons of NATURAL LIGHT. The owner has invested over $30K in LED lighting & many other upgrades to make this home extra bright, airy and open. Located in a very peaceful, restful, tropical-like setting, with fountains and plenty of trees and tropical landscaping, the GATED, secure SUN BAY CLUB is a quiet, well-established, LAKE FRONT community, with a huge lakeside pool, tennis court, and a relaxing lakeside seating area around the fire pit. This unit is situated toward the back side of the community, away from the main entrance gate, and within a stone’s throw of the POOL and partial lake view of beautiful LAKE DESTINY. There's AMPLE PARKING for you and your guests! CONDO FEE INCLUDES: CABLE & HIGH-SPEED SPECTRUM INTERNET, building and exterior grounds maintenance, pool and amenities, common areas maintenance, reserves funding, master insurance policy coverage and more. BRAND NEW TILE ROOFS were installed 2024. SELLER WILL PAY THE REMAINING SPECIAL ASSESSMENT IN FULL AT CLOSING with accepted offer! CENTRALLY LOCATED in the Maitland Center, just across from the RDV Sports Complex (now Genesis Health), minutes from I-4, shopping, dining, the entertainment parks, and the beaches. So much to offer you in this community and this beautiful one-of-a-kind condo unit. Call today to view it, then come back soon and call it HOME!

3 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

NEWLY ‘ACTIVE’. . . . RENEWED AND REFRESHED . . . AND BACK ON THE MARKET WITH EXCITING NEW UPDATES! NEWLY PAINTED INTERIOR, NEWLY UPDATED MASTER BATH, AND FRESH FRONT AND REAR EXTERIOR UPDATING! If you thought all condos were pretty much the same boring 4 walls, THINK AGAIN! This secluded little jewel is UNIQUE and CONTEMPORARY with TONS OF CHARACTER, and VERY AFFORDABLE! Grab your morning coffee and walk the few steps from your kitchen/patio down TO THE LAKE and soak up a few peaceful moments before starting the rush of your day! This amazing 3 BEDROOM, 2 BATH, OPEN FLOOR PLAN offers 2 MASTER SUITES, plus a 3rd bedroom that could easily be used as an office, den, or playroom. A wood-burning FIREPLACE is at the center of the main living area. The LARGE KITCHEN has plenty of room for an eat-in table. EVERY BEDROOM HAS A SLIDING GLASS DOOR to the outside patio, with beautiful OVER-SIZED WINDOWS, letting in tons of NATURAL LIGHT. The owner has invested over $30K in LED lighting & many other upgrades to make this home extra bright, airy and open. Located in a very peaceful, restful, tropical-like setting, with fountains and plenty of trees and tropical landscaping, the GATED, secure SUN BAY CLUB is a quiet, well-established, LAKE FRONT community, with a huge lakeside pool, tennis court, and a relaxing lakeside seating area around the fire pit. This unit is situated toward the back side of the community, away from the main entrance gate, and within a stone’s throw of the POOL and partial lake view of beautiful LAKE DESTINY. There's AMPLE PARKING for you and your guests! CONDO FEE INCLUDES: CABLE & HIGH-SPEED SPECTRUM INTERNET, building and exterior grounds maintenance, pool and amenities, common areas maintenance, reserves funding, master insurance policy coverage and more. BRAND NEW TILE ROOFS were installed 2024. SELLER WILL PAY THE REMAINING SPECIAL ASSESSMENT IN FULL AT CLOSING with accepted offer! CENTRALLY LOCATED in the Maitland Center, just across from the RDV Sports Complex (now Genesis Health), minutes from I-4, shopping, dining, the entertainment parks, and the beaches. So much to offer you in this community and this beautiful one-of-a-kind condo unit. Call today to view it, then come back soon and call it HOME!

1000 Winderley Place Unit 143, Maitland

$240,000

Welcome to Sun Bay Club, a hidden gem in the heart of Maitland. This spacious, Bright and Airy 2/2 is move in ready as is, or add your personal touches. Through the Double-Door entry you will find the foyer with a handy Storage Closet. The Foyer overlooks the sunken Living Room with a Wood Burning Fireplace flanked by a niche and Wet Bar, and Sliders to the 21' x 6' Enclosed All Season Patio overlooking the serene Pond outside with a soothing Fountain. The spacious Dining Area is Nestled in the corner. To the right of the Foyer is the Kitchen that offers lots of Counter and Storage Space and opens to the Dining Area. Down the hall you will find the Spacious Primary Bedroom that has Sliders to the Enclosed Patio, an En-Suite Bathroom with Dual Sinks, Art Deco inspired Curved Shower with Glass Block and a Large Walk-in Closet. Head down the hall and find the Laundry Closet (Washer/Dryer INCLUDED) and the Guest Bath with Tub/Shower combo with access to Bedroom 2, another spacious room with lots of closet space and Sliders overlooking the Private Entry. A/C Compressor and Water Heater replaced 2024. Sun Bay is Maitland’s best kept secret on the shores of Lake Destiny. Amenities include, CABLE TV and INTERNET INCLUDED in the fees, a Lakefront Pool & Spa, Community Boat Ramp, Tennis Courts, Car Wash Spot and Dog Park. BRAND NEW TILE ROOFS and GUTTERS were just installed. This community offers a luxurious feel with its many ponds and fountains. Located near Maitland Office Park with easy access to I-4, 414 Maitland Exchange, RDV Sportsplex, Hospitals, Shopping and so much more! Reach out today to set up a showing.

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

Welcome to Sun Bay Club, a hidden gem in the heart of Maitland. This spacious, Bright and Airy 2/2 is move in ready as is, or add your personal touches. Through the Double-Door entry you will find the foyer with a handy Storage Closet. The Foyer overlooks the sunken Living Room with a Wood Burning Fireplace flanked by a niche and Wet Bar, and Sliders to the 21' x 6' Enclosed All Season Patio overlooking the serene Pond outside with a soothing Fountain. The spacious Dining Area is Nestled in the corner. To the right of the Foyer is the Kitchen that offers lots of Counter and Storage Space and opens to the Dining Area. Down the hall you will find the Spacious Primary Bedroom that has Sliders to the Enclosed Patio, an En-Suite Bathroom with Dual Sinks, Art Deco inspired Curved Shower with Glass Block and a Large Walk-in Closet. Head down the hall and find the Laundry Closet (Washer/Dryer INCLUDED) and the Guest Bath with Tub/Shower combo with access to Bedroom 2, another spacious room with lots of closet space and Sliders overlooking the Private Entry. A/C Compressor and Water Heater replaced 2024. Sun Bay is Maitland’s best kept secret on the shores of Lake Destiny. Amenities include, CABLE TV and INTERNET INCLUDED in the fees, a Lakefront Pool & Spa, Community Boat Ramp, Tennis Courts, Car Wash Spot and Dog Park. BRAND NEW TILE ROOFS and GUTTERS were just installed. This community offers a luxurious feel with its many ponds and fountains. Located near Maitland Office Park with easy access to I-4, 414 Maitland Exchange, RDV Sportsplex, Hospitals, Shopping and so much more! Reach out today to set up a showing.

1000 Winderley Place Unit 122, Maitland

$1,700,000

One or more photo(s) has been virtually staged. Short Sale. This home needs love ...Located on the private 57-acre ski lake, Lake Seminary, this 8-bedroom, 7-bathroom home offers breathtaking views and quick access to Winter Park, I-4, and Maitland Town Center. Featuring two master suites and a flexible use suite with a separate entrance, the home boasts a grand entry with double staircases and soaring 24-foot ceilings. The chef’s kitchen is designed for entertaining, complete with granite counters, three dishwashers, double ovens, a warming drawer, and a hidden butler’s pantry. The living room showcases coffered ceilings, a gas fireplace, and sliding glass doors that open to the screened outdoor space. Built with foam-insulated concrete tilt-wall construction, this home includes Smart House technology, a Cat-5E LAN system, audio-visual wiring, a four-zoned TRANE HVAC system. Additional highlights include a theater room with a wet bar, designed as a hurricane-safe room, and multiple laundry rooms for convenience. Outside, the covered pool area features a 30x39 ft pool and heated spa all overlooking the lake.

9 Beds ⋅ 7 Baths ⋅ Stonehill SubDv. ⋅ 32751 Zip Code

One or more photo(s) has been virtually staged. Short Sale. This home needs love ...Located on the private 57-acre ski lake, Lake Seminary, this 8-bedroom, 7-bathroom home offers breathtaking views and quick access to Winter Park, I-4, and Maitland Town Center. Featuring two master suites and a flexible use suite with a separate entrance, the home boasts a grand entry with double staircases and soaring 24-foot ceilings. The chef’s kitchen is designed for entertaining, complete with granite counters, three dishwashers, double ovens, a warming drawer, and a hidden butler’s pantry. The living room showcases coffered ceilings, a gas fireplace, and sliding glass doors that open to the screened outdoor space. Built with foam-insulated concrete tilt-wall construction, this home includes Smart House technology, a Cat-5E LAN system, audio-visual wiring, a four-zoned TRANE HVAC system. Additional highlights include a theater room with a wet bar, designed as a hurricane-safe room, and multiple laundry rooms for convenience. Outside, the covered pool area features a 30x39 ft pool and heated spa all overlooking the lake.

125 Stone Hill Drive, Maitland

$239,000

PRICE IMPROVEMENT...Lakefront Condo in Maitland’s Jupiter Building – First-Floor Unit with access to Scenic Lake Views. Welcome to lakefront living in the desirable Lake Maitland Terrace community! This beautifully maintained first-floor, 2-bedroom, 1.5-bath condo in the Jupiter Building offers the perfect blend of comfort, convenience, and lifestyle. The updated kitchen features maple cabinetry, granite countertops, and a new stainless steel refrigerator. Enjoy refreshed bathrooms, custom plantation shutters, and the convenience of an in-unit washer and dryer. Natural light pours in through large high-efficiency Kolbe double-pane windows, and the front porch offers a peaceful partial view of Lake Maitland, perfect for enjoying your morning coffee or unwinding after a day on the water. The entire community has undergone recent updates, including a new roof installed in 2023 and fresh exterior paint in 2025, adding both style and peace of mind to this mid-century modern gem. Resort-style amenities include a lakefront swimming pool, private fishing dock, easy access for kayaking and paddleboarding, clubhouse with a wraparound porch, shuffleboard courts, bicycle storage, and a car wash station. Occasional boat slips are available for residents at an additional cost. The HOA includes water, sewer, valet-style garbage collection, and mail delivery directly to your door. The community is professionally managed with an on-site manager and maintenance team, and EV charging permits may be requested for your assigned parking spot. Located just minutes from Winter Park, Park Avenue, Rollins College, and top dining destinations like Luke’s and Antonio’s, with easy access to downtown Orlando, Orlando International Airport, and major Central Florida attractions. If you’ve been searching for a lake-access condo in Central Florida, this is your chance. Schedule your private tour today and experience the best of lakefront living in Maitland, FL!

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

PRICE IMPROVEMENT...Lakefront Condo in Maitland’s Jupiter Building – First-Floor Unit with access to Scenic Lake Views. Welcome to lakefront living in the desirable Lake Maitland Terrace community! This beautifully maintained first-floor, 2-bedroom, 1.5-bath condo in the Jupiter Building offers the perfect blend of comfort, convenience, and lifestyle. The updated kitchen features maple cabinetry, granite countertops, and a new stainless steel refrigerator. Enjoy refreshed bathrooms, custom plantation shutters, and the convenience of an in-unit washer and dryer. Natural light pours in through large high-efficiency Kolbe double-pane windows, and the front porch offers a peaceful partial view of Lake Maitland, perfect for enjoying your morning coffee or unwinding after a day on the water. The entire community has undergone recent updates, including a new roof installed in 2023 and fresh exterior paint in 2025, adding both style and peace of mind to this mid-century modern gem. Resort-style amenities include a lakefront swimming pool, private fishing dock, easy access for kayaking and paddleboarding, clubhouse with a wraparound porch, shuffleboard courts, bicycle storage, and a car wash station. Occasional boat slips are available for residents at an additional cost. The HOA includes water, sewer, valet-style garbage collection, and mail delivery directly to your door. The community is professionally managed with an on-site manager and maintenance team, and EV charging permits may be requested for your assigned parking spot. Located just minutes from Winter Park, Park Avenue, Rollins College, and top dining destinations like Luke’s and Antonio’s, with easy access to downtown Orlando, Orlando International Airport, and major Central Florida attractions. If you’ve been searching for a lake-access condo in Central Florida, this is your chance. Schedule your private tour today and experience the best of lakefront living in Maitland, FL!

1140 S Orlando Avenue Unit J6, Maitland

$585,000

Welcome to your dream home in the exclusive gated community of The Enclave at Maitland, affectionately known as Montacino. This meticulously maintained Spanish-style town-home offers a harmonious blend of elegance and comfort, designed to cater to your every need. As you enter this large, 4BR 3.5BA home you step through the inviting Foyer where you're greeted by an expansive open floor plan bathed in natural light. The Living Room, adorned with large windows, flows effortlessly into the spacious Dining Room, creating an ideal space for both relaxation and entertaining. Culinary enthusiasts will delight in the beautifully appointed Kitchen, featuring 42-inch cabinets with intricate rope crown molding, gleaming granite counter tops, a convenient breakfast bar, and stainless steel appliances. The diagonally laid tile floor adds a touch of sophistication to this culinary haven. Imagine starting your day in the cozy Breakfast Nook, savoring your morning coffee while overlooking the charming pavered courtyard—a serene spot to enjoy the morning sun. One of the home's standout features is the Primary Bedroom conveniently located on the main floor. This tranquil retreat offers views of the Courtyard and boasts a luxurious en-suite bathroom complete with a spacious soaking tub and comfort-height vanities topped with granite. Venture upstairs to discover a Second Primary Bedroom, equally impressive, featuring its own en-suite bathroom with similar upscale finishes. Two additional well-appointed Bedrooms provide flexibility and comfort, each offering picturesque views of Lake Charity. A full bathroom with a tub-shower combination serves these bedrooms, ensuring convenience for family or guests. For added ease, the Laundry Room is thoughtfully situated on the second floor, streamlining your daily routines. Car enthusiasts and hobbyists will appreciate the oversized two-car attached garage, offering an extra five feet of space perfect for storage or a workshop area. As a resident of this exceptional community, you'll have access to a sparkling resort-style pool nestled by the serene shores of Lake Charity. With easy access to Maitland Boulevard and I-4, as well as a plethora of local shopping, offices, and dining options, this location offers the perfect blend of convenience and tranquility. The added security of a gated community provides peace of mind, allowing you to fully enjoy your surroundings. Don't miss the opportunity to make this exquisite town-home your own. Experience the perfect fusion of luxury, comfort, and convenience in the heart of Maitland.

4 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Welcome to your dream home in the exclusive gated community of The Enclave at Maitland, affectionately known as Montacino. This meticulously maintained Spanish-style town-home offers a harmonious blend of elegance and comfort, designed to cater to your every need. As you enter this large, 4BR 3.5BA home you step through the inviting Foyer where you're greeted by an expansive open floor plan bathed in natural light. The Living Room, adorned with large windows, flows effortlessly into the spacious Dining Room, creating an ideal space for both relaxation and entertaining. Culinary enthusiasts will delight in the beautifully appointed Kitchen, featuring 42-inch cabinets with intricate rope crown molding, gleaming granite counter tops, a convenient breakfast bar, and stainless steel appliances. The diagonally laid tile floor adds a touch of sophistication to this culinary haven. Imagine starting your day in the cozy Breakfast Nook, savoring your morning coffee while overlooking the charming pavered courtyard—a serene spot to enjoy the morning sun. One of the home's standout features is the Primary Bedroom conveniently located on the main floor. This tranquil retreat offers views of the Courtyard and boasts a luxurious en-suite bathroom complete with a spacious soaking tub and comfort-height vanities topped with granite. Venture upstairs to discover a Second Primary Bedroom, equally impressive, featuring its own en-suite bathroom with similar upscale finishes. Two additional well-appointed Bedrooms provide flexibility and comfort, each offering picturesque views of Lake Charity. A full bathroom with a tub-shower combination serves these bedrooms, ensuring convenience for family or guests. For added ease, the Laundry Room is thoughtfully situated on the second floor, streamlining your daily routines. Car enthusiasts and hobbyists will appreciate the oversized two-car attached garage, offering an extra five feet of space perfect for storage or a workshop area. As a resident of this exceptional community, you'll have access to a sparkling resort-style pool nestled by the serene shores of Lake Charity. With easy access to Maitland Boulevard and I-4, as well as a plethora of local shopping, offices, and dining options, this location offers the perfect blend of convenience and tranquility. The added security of a gated community provides peace of mind, allowing you to fully enjoy your surroundings. Don't miss the opportunity to make this exquisite town-home your own. Experience the perfect fusion of luxury, comfort, and convenience in the heart of Maitland.

1161 Charming Street, Maitland

$415,000

Stunning 3-bedroom, 2 and ½-Bath townhome located in the highly sought-after Park Maitland community. This spacious residents features an open floor plan including 42 inch maple cabinets in the kitchen, maple wood flooring in the main living area, elegant finishes like stainless steel appliances, and abundant natural light throughout. The oversized master suite offers a private retreat, while the beautiful fenced in backyard with a covered walkway from the 2-car garage to the main home provides ample space for outdoor entertainment. Ideally located near top-rated schools, shopping, and dining, this home combines convenience with comfort. Don’t miss out on the opportunity to make this property your own! Schedule a viewing today.

3 Beds ⋅ 3 Baths ⋅ Park Maitland Villas SubDv. ⋅ 32751 Zip Code

Stunning 3-bedroom, 2 and ½-Bath townhome located in the highly sought-after Park Maitland community. This spacious residents features an open floor plan including 42 inch maple cabinets in the kitchen, maple wood flooring in the main living area, elegant finishes like stainless steel appliances, and abundant natural light throughout. The oversized master suite offers a private retreat, while the beautiful fenced in backyard with a covered walkway from the 2-car garage to the main home provides ample space for outdoor entertainment. Ideally located near top-rated schools, shopping, and dining, this home combines convenience with comfort. Don’t miss out on the opportunity to make this property your own! Schedule a viewing today.

2250 Park Maitland Court, Maitland

$2,150,000

Discover a once-in-a-lifetime chance to own nearly a half acre of prime lakefront property on Lake Maitland, the largest of the Winter Park Chain of Lakes. Nestled in a serene alcove, this secluded setting is surrounded by multimillion-dollar homes and new custom construction, offering endless possibilities for creating your dream estate. The value of this property lies in the land, making it the perfect canvas for designing the ultimate lakefront retreat. Renovate the existing home or start fresh to craft a residence that meets your every desire. A covered boat dock with lift ensures easy access to the Chain of Lakes, where you can enjoy boating, waterskiing, wakeboarding, paddleboarding, and fishing. The property also features a lakeside pool with spa and a concrete seawall to protect and enhance your waterfront experience. This tranquil neighborhood is graced with towering oak trees and winding roads that create a picturesque setting. Located just minutes from downtown Winter Park, you’ll enjoy fine dining, boutique shopping, and cultural experiences along Park Avenue. The property is zoned for top-rated public schools and conveniently close to everyday necessities. Lake Maitland is not just a home — it’s a lifestyle. A short boat ride takes you to the Winter Park Racquet Club, a premier destination for dining and social events. Don’t miss this extraordinary opportunity to embrace the luxury and leisure of lakefront living on the prestigious Winter Park Chain of Lakes.

3 Beds ⋅ 3 Baths ⋅ Lake Maitland Point X/8 Lot 1 SubDv. ⋅ 32751 Zip Code

Discover a once-in-a-lifetime chance to own nearly a half acre of prime lakefront property on Lake Maitland, the largest of the Winter Park Chain of Lakes. Nestled in a serene alcove, this secluded setting is surrounded by multimillion-dollar homes and new custom construction, offering endless possibilities for creating your dream estate. The value of this property lies in the land, making it the perfect canvas for designing the ultimate lakefront retreat. Renovate the existing home or start fresh to craft a residence that meets your every desire. A covered boat dock with lift ensures easy access to the Chain of Lakes, where you can enjoy boating, waterskiing, wakeboarding, paddleboarding, and fishing. The property also features a lakeside pool with spa and a concrete seawall to protect and enhance your waterfront experience. This tranquil neighborhood is graced with towering oak trees and winding roads that create a picturesque setting. Located just minutes from downtown Winter Park, you’ll enjoy fine dining, boutique shopping, and cultural experiences along Park Avenue. The property is zoned for top-rated public schools and conveniently close to everyday necessities. Lake Maitland is not just a home — it’s a lifestyle. A short boat ride takes you to the Winter Park Racquet Club, a premier destination for dining and social events. Don’t miss this extraordinary opportunity to embrace the luxury and leisure of lakefront living on the prestigious Winter Park Chain of Lakes.

451 Northwind Road, Maitland

$235,000

This is the only Lake Maitland Terrace condo available with multi-million $$$ Lake Maitland LAKEFRONT views from both bedrooms!!! And partial lakefront view from front screened-in porch! This updated condo offers stunning lakefront views at the iconic Lake Maitland Terrace! Located on the second floor, this corner unit is situated in the last building down by the lake. The screened-in front porch is ideal for relaxing while overlooking the expansive lakefront campus, which includes a beautiful pool, fishing dock, putting green, and shuffleboard courts. Upon entering, you will be welcomed by a newly painted interior and brand new carpet in the secondary bedroom. The common areas feature luxury vinyl plank flooring. The living room boasts two large windows that allow plenty of natural light and opens up to the dining area and the adjacent kitchen, which is equipped with neutral cabinets and white tile floors & backsplash. The owner's suite includes a walk-in closet and an attached renovated half bath, along with a lovely view of the lake. The second bedroom also offers a lake view and includes a closet with a stackable washer and dryer. There is 1 designated parking spot, and additional guest parking as needed. New roof 2023/24. The community also has an enclosed bicycle garage, convenient laundry facilities, and kayak and paddleboard racks. Super convenient location – walk to Enzian and Lake Lily, 5-minute drive to Winter Park’s downtown, and easy access to I-4.

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

This is the only Lake Maitland Terrace condo available with multi-million $$$ Lake Maitland LAKEFRONT views from both bedrooms!!! And partial lakefront view from front screened-in porch! This updated condo offers stunning lakefront views at the iconic Lake Maitland Terrace! Located on the second floor, this corner unit is situated in the last building down by the lake. The screened-in front porch is ideal for relaxing while overlooking the expansive lakefront campus, which includes a beautiful pool, fishing dock, putting green, and shuffleboard courts. Upon entering, you will be welcomed by a newly painted interior and brand new carpet in the secondary bedroom. The common areas feature luxury vinyl plank flooring. The living room boasts two large windows that allow plenty of natural light and opens up to the dining area and the adjacent kitchen, which is equipped with neutral cabinets and white tile floors & backsplash. The owner's suite includes a walk-in closet and an attached renovated half bath, along with a lovely view of the lake. The second bedroom also offers a lake view and includes a closet with a stackable washer and dryer. There is 1 designated parking spot, and additional guest parking as needed. New roof 2023/24. The community also has an enclosed bicycle garage, convenient laundry facilities, and kayak and paddleboard racks. Super convenient location – walk to Enzian and Lake Lily, 5-minute drive to Winter Park’s downtown, and easy access to I-4.

1140 S Orlando Avenue Unit K15, Maitland

$632,500

A Lakefront Masterpiece, this 3-bedroom, 2-bathroom pool home is a gem for those who demand the finest in life. Nestled in the heart of Maitland - From the moment you arrive, the all-new paver driveway and front porch make a striking first impression, setting the stage for the pristine interiors that await. Outside, the zen-inspired backyard redefines tranquility, featuring a new resurfaced crystal-clear pool, a chic pergola, and breathtaking views of the lake. This private oasis is perfect for morning meditations, sunset gatherings, or simply indulging in the serenity of waterfront living.

3 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 1 Rep SubDv. ⋅ 32751 Zip Code

A Lakefront Masterpiece, this 3-bedroom, 2-bathroom pool home is a gem for those who demand the finest in life. Nestled in the heart of Maitland - From the moment you arrive, the all-new paver driveway and front porch make a striking first impression, setting the stage for the pristine interiors that await. Outside, the zen-inspired backyard redefines tranquility, featuring a new resurfaced crystal-clear pool, a chic pergola, and breathtaking views of the lake. This private oasis is perfect for morning meditations, sunset gatherings, or simply indulging in the serenity of waterfront living.

2631 Falmouth Road, Maitland

$650,000

This spacious block home in Dommerich Estates sits on a 0.29-acre lot and offers endless potential for renovation or a complete rebuild. Built by Charlie Clayton, the home features a brick exterior, an oversized two-car garage, and a versatile layout. The original eat-in kitchen connects to a great room that leads to a large Florida room with windows overlooking the pool and a generously sized backyard. The master suite includes terrazzo floors, a walk-in closet, and a shared bathroom that connects to an office, which then leads to a fourth bedroom with its own walk-in closet. Two additional bedrooms, both generously sized, share a second bathroom. A separate family room boasts a brick fireplace, exposed beams, and built-in seating with storage. The backyard offers plenty of space alongside the pool, perfect for entertaining or enjoying the outdoors. Located within walking distance to Dommerich Elementary and Maitland Middle and zoned for Winter Park High School, this property is also near Maitland Community Boardwalk Park and offers optional access to Lake Minnehaha, part of the Winter Park Chain of Lakes, for a nominal annual fee.

4 Beds ⋅ 2 Baths ⋅ Dommerich Ests 1st Add SubDv. ⋅ 32751 Zip Code

This spacious block home in Dommerich Estates sits on a 0.29-acre lot and offers endless potential for renovation or a complete rebuild. Built by Charlie Clayton, the home features a brick exterior, an oversized two-car garage, and a versatile layout. The original eat-in kitchen connects to a great room that leads to a large Florida room with windows overlooking the pool and a generously sized backyard. The master suite includes terrazzo floors, a walk-in closet, and a shared bathroom that connects to an office, which then leads to a fourth bedroom with its own walk-in closet. Two additional bedrooms, both generously sized, share a second bathroom. A separate family room boasts a brick fireplace, exposed beams, and built-in seating with storage. The backyard offers plenty of space alongside the pool, perfect for entertaining or enjoying the outdoors. Located within walking distance to Dommerich Elementary and Maitland Middle and zoned for Winter Park High School, this property is also near Maitland Community Boardwalk Park and offers optional access to Lake Minnehaha, part of the Winter Park Chain of Lakes, for a nominal annual fee.

1720 Algonquin Trail, Maitland

$312,000

Totally updated gorgeous condo. Once inside you will see a designer inspired beautiful home! This light and bright home is ready to move into with too many upgrades to list. The Kitchen is a gourmet's delight featuring 42-inch cabinets, a center island, built in oven, built in cook top and stone counters. Don't worry when you entertain as this kitchen opens up to the dining and family room, making it perfect for entertaining. The family room features a vaulted ceiling, a wood burning fireplace, wood floors and plenty of light! The enclosed patio gives you even more space for entertaining and has a beautiful view of the fountain and water. The guest bedroom (currently being used as a den) Is large and spacious featuring a large closet as well. The adjoining guest bath is totally updated in beautiful neutral colors. The primary bedroom is just off from the family room and is large and spacious. Once you enter into the primary ensuite you will feel as though you have walked into a spa. Double vanities and the Shower has got to be seen to be believed Imagine a large walk-in shower with a skylight? You may never want to leave the peace and tranquility of this ensuite bath. A very large walk-in closet will give you plenty of space. Sun Bay club located in the heart of Maitland and has got to be one of the best kept secrets in Maitland. The HOA fee includes all the exterior maintenance, roof, common areas, pool, cable as well as high speed internet and wi-fi. Conveniently located near Maitland Center, I-4, the 414 and is close to medical, shopping, restaurants and much more. Make your appointment today to see this gorgeous home!

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

Totally updated gorgeous condo. Once inside you will see a designer inspired beautiful home! This light and bright home is ready to move into with too many upgrades to list. The Kitchen is a gourmet's delight featuring 42-inch cabinets, a center island, built in oven, built in cook top and stone counters. Don't worry when you entertain as this kitchen opens up to the dining and family room, making it perfect for entertaining. The family room features a vaulted ceiling, a wood burning fireplace, wood floors and plenty of light! The enclosed patio gives you even more space for entertaining and has a beautiful view of the fountain and water. The guest bedroom (currently being used as a den) Is large and spacious featuring a large closet as well. The adjoining guest bath is totally updated in beautiful neutral colors. The primary bedroom is just off from the family room and is large and spacious. Once you enter into the primary ensuite you will feel as though you have walked into a spa. Double vanities and the Shower has got to be seen to be believed Imagine a large walk-in shower with a skylight? You may never want to leave the peace and tranquility of this ensuite bath. A very large walk-in closet will give you plenty of space. Sun Bay club located in the heart of Maitland and has got to be one of the best kept secrets in Maitland. The HOA fee includes all the exterior maintenance, roof, common areas, pool, cable as well as high speed internet and wi-fi. Conveniently located near Maitland Center, I-4, the 414 and is close to medical, shopping, restaurants and much more. Make your appointment today to see this gorgeous home!

1000 Winderley Place Unit 241, Maitland