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$235,000
3 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo Ph D SubDv. ⋅ 32751 Zip Code
Now is your chance...3 BR 3 BA Townhome great location close to I-4 and 17/92, Community pool, newer roof (4 yrs) Quiet dead end Street Enter through gate or garage door. Back door opens to laundry room with brand new water heater, brand new garage door opener and a washer and dryer, then into the galley kitchen with a new stainless steel fridge. You have a dining room living room combo and one bedroom and full bath on first floor. Lots of closet space. Front door opens to wooded area and small front porch. Upstairs there are 2 bedroom suites. One bath has shower one with tub. One offers a balcony with lake view overlooking green area. Big closets. Brand new carpet staircase and upstairs bedrooms. This home is close to fine dining restaurants, shopping, hospital, winter Park Village and downtown Maitland Lake Lily and 2 farmers markets. Nice quiet walkable neighborhood.

1550 Gulfview Drive Unit 444, Maitland
$448,500
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code
Seller to pay up to one year of HOA! Wake up to shimmering lake views and unwind each evening with breathtaking Florida sunsets in this beautifully refreshed 2-bedroom, 2-bathroom condo. From the moment you step off the elevator, you’re welcomed into a light-filled, open-concept living space highlighted by oversized glass sliding doors that lead to a private enclosed patio—seamlessly blending indoor and outdoor living. The kitchen is both bright and inviting, featuring upgraded cabinetry, a spacious eat-in area, and a large island designed for effortless entertaining. Thoughtful updates throughout include upgraded flooring, brand-new carpet installed just six months ago, and a newer AC unit replaced two years ago for added comfort and peace of mind. Custom-tailored curtains complete the space with a refined, polished finish. cThe primary suite offers a quiet, private retreat with its own bath, while the split-bedroom layout ensures comfort and privacy for guests. Life at The Moorings is centered around a relaxed, lakeside lifestyle—complete with a community pool, heated spa, clubhouse, lushly landscaped grounds, and direct access to Lake Maitland on the Winter Park Chain of Lakes. Spend your days on the lakefront dock or hosting poolside gatherings, then enjoy the convenience of walking to local favorites like Luke’s and Antonio’s or exploring Maitland’s newly designed downtown with green spaces, farmers markets, and vibrant community events.

204 Quayside Circle Unit 504, Maitland
$1,090,000
5 Beds ⋅ 5 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code
HARD TO FIND SKI LAKEFRONT! Classic traditional beauty – ready for a lucky buyer to make home. Stunning water & sunset views over Lake of the Woods from most living areas. Enter into the impressive foyer with curved stairway; light & bright large formal rooms with French doors to wrap around covered porch; Large open kitchen, wood cabinets, granite tops, stainless appliances and breakfast nook to sip coffee and bird watch! Inviting family room with fireplace and custom built in surrounds. First level guest suite and full bath; elevator serves to 2nd level huge Master suite, with open deck and lake views; Master bath, dual vanities, Jacuzzi tub and shower, walk in closet. 2 additional large sunny bedrooms share Jack & Jill bath, 3rd upstairs bedroom is ensuite with a large walk in closet. Lovely landscape provides privacy and beauty. New boathouse and dock are ready for action! Super side entry 3 car garage, storage, huge utility room. Survey, pool plan available. Seminole County Schools PLUS excellent Private Schools within a few miles. Neutral colors, tile roof. Bring your water skis, knee boards, fishing poles & kayaks! Sold As-is; seller may consider decor credit with acceptable offer!

1256 Wellington Terrace, Maitland
$130,000
1 Beds ⋅ 1 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code
Virtually Staged. Water views, major system upgrades, and the best value in Visconti. This beautifully updated 1-bedroom, 1-bath condo is priced $16,000 below the next comparable unit in the community and features over $15,000 in recent improvements, including a brand-new Goodman 2-ton 14.3 SEER HVAC system (2025), a new water heater with an expansion tank (2026), and stylish shaker kitchen cabinets (2025). Enjoy tranquil pond views from both the living room and bedroom, with a large sliding glass door leading to your private balcony. The open-concept layout offers abundant natural light, built-in shelving, and a functional floor plan designed for comfortable everyday living. A separate laundry room adds extra convenience and storage. Located within the gated Visconti community, residents enjoy resort-style amenities including two swimming pools, a fitness center, clubhouse, tennis and basketball courts, and scenic paths. HOA fees include water, sewer, and trash service. Conveniently located just minutes from I-4, Downtown Orlando, Winter Park, Altamonte Springs, major employers, shopping, dining, Walt Disney World, Universal Orlando, and Orlando International Airport. Whether you're a first-time homebuyer, downsizing, or seeking a low-maintenance investment property, this move-in-ready condo offers exceptional value and location. Mortgage savings may be available for buyers of this listing.

1275 Lake Shadow Circle Unit 13206, Maitland
$365,000
2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
This condo was completely renovated in 2023 and is located in one of the best spots within the complex. Positioned directly on the Winter Park chain of lakes, it offers excellent access to everything Winter Park and Maitland have to offer. Residents enjoy being within walking distance to a variety of restaurants and shopping, creating an ideal blend of convenience and lifestyle. This unique corner unit features great views and a screened-in porch on the first floor, perfect for enjoying the surroundings. Because it is a corner residence, the condo is filled with lovely natural light from multiple windows, enhancing the open feel. Its location also provides easy access to the pool area for added everyday convenience. Inside, the condo offers two full baths and extensive upgrades throughout. Raised ceilings contribute to the spacious atmosphere, while newer electrical, plumbing, and a hot water heater provide peace of mind. The home includes newer full-sized appliances, custom cabinetry, granite countertops, newer flooring, custom closets, and an in-unit washer and dryer. Residents enjoy lake access with beautiful views and the community amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. With renovations completed in 2023, the condo features modern finishes and systems that feel fresh and move-in ready.

1140 S Orlando Avenue Unit F-1, Maitland
$364,000
3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
BELOW APPRAISAL + SELLER OFFERING INTEREST RATE BUY-DOWN with acceptable offer. /// Why settle for "standard" when you can own a designer-caliber home in Maitland with a lower monthly payment? Priced at $369,000—well below the recent $384K appraisal—this high-end unit offers instant equity. *LIFESTYLE & LOCATION /// RECLAIM YOUR TIME: Just 10 minutes to Downtown Orlando or Winter Park. PET FRIENDLY: Montecino is a gated, pet-loving community. LAKE CHARITY: Enjoy a scenic walk right outside your door. Maintenance-free living with a resort-style pool and gated security. *UPGRADES & VALUE /// MECHANICALLY NEW: New HVAC (Jan 2025), Bosch dishwasher, and 2026 fridge/microwave. DESIGNER FINISHES: Engineered hardwoods, fresh paint, and designer lighting. HOA BONUS: Monthly dues include High-Speed Internet, WiFi, and expanded TV/Streaming.*PEACE OF MIND /// Home just passed INSPECTION. Between the verified value, mechanical updates, and potential interest rate buy-down, this is the most secure and affordable luxury entry in Maitland. Also available for rent at $2500/month. Seller seeking a long-term, high-quality tenant.

1321 Benevolent Street, Maitland
$689,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills 2 Nd Add SubDv. ⋅ 32751 Zip Code
Under contract-accepting backup offers. Priced below Appraised Value — and the seller is ready to move. This classic 4-bedroom, 2.5-bath Maitland pool home sits on a spacious quarter-to-half-acre lot with peaceful lake views and delivers 3,000 square feet of open, comfortable living. The updated kitchen and open floor plan make the interior as functional as it is inviting, but the real showstopper is outside — a sparkling pool (Resurface 2025) and generous outdoor living area with a lake backdrop that makes every evening feel like a retreat. The big-ticket items are already handled: 7-year roof, 7-year AC, updated plumbing, and a fully paid-off solar system that virtually eliminates your monthly electric bill — and under Florida law, it won't raise your property taxes. Zoned for top-rated schools and just minutes to Winter Park's dining, shopping, and culture. This is a home with more value than the price tag suggests. Motivated seller. Bring your

2514 Tuscarora Trail, Maitland
$690,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code
Luxury lakefront living at its finest awaits at "The Moorings" on Lake Maitland Chain of Lakes. Perfectly positioned on the first floor, this stunning two-bedroom, two-bath residence offers breathtaking lake views from nearly every room, creating a serene and sophisticated backdrop for everyday living. Completely renovated with impeccable attention to detail, the home features designer epoxy flooring throughout the main living areas and luxury statement lighting that elevates the space with warmth and style. The living room invites relaxation with a sleek electric fireplace and expansive glass sliders that open to an extra-large lanai overlooking Lake Maitland—an ideal setting for morning coffee, evening sunsets, or effortless entertaining. The state-of-the-art chef’s kitchen is a true showpiece, thoughtfully designed for both beauty and function. It includes modern quartz countertops, a smart refrigerator with TV, with AI vision that updates your shopping list, planning and interactive features, a wine refrigerator, new stainless steel appliances, a vented hood, cooktop with pot filler, Bosch dishwasher, and a double oven with convection microwave combination and convection oven—perfect for hosting and everyday luxury. A discreet pantry closet houses a stackable washer and dryer, seamlessly integrating convenience into the design. The primary suite is a tranquil retreat with stunning lake views and a custom walk-in closet system complete with jewelry drawer, laundry bins, and generous storage. The spa-inspired primary bath features dual quartz vanities, a frameless glass shower, and a luxurious rain shower head, while the high-end bidet toilet automatically opens upon entry for an added touch of modern indulgence. The guest suite is equally impressive, featuring a custom Murphy bed with integrated storage and desk, dresser, television, and elegant glass closet doors. The adjacent guest bath has been fully reimagined as a spa sanctuary with a jetted soaking tub, designer tile, a custom light-up mirror, and new quartz top vanity. Storage is abundant throughout the home, including a coat closet, a hidden hideaway closet concealed behind a custom bookcase, and thoughtfully designed built-ins that maximize space without sacrificing style. Residents of "The Moorings" enjoy exceptional community amenities, including a resort-style pool with spa and a clubhouse ideal for private parties and social gatherings. The community is impeccably maintained, featuring new exterior paint and seal, a newer roof, and beautifully maintained landscaping, reflecting true pride of ownership. Additional features include a security system, smart thermostat, newer AC, and newer appliances, offering peace of mind and energy efficiency. For outdoor enthusiasts, the community allows storage for kayaks and paddleboards, with boat slip #16 available for rent, providing direct access to the Chain of Lakes lifestyle. Ideally located near Lake Lily’s Farmers Market, popular restaurants, extensive shopping, bus routes, and with easy access to I-4, this home is also zoned for top-rated A+ schools—blending luxury, convenience, and lifestyle into one exceptional offering. This is more than a home—it’s a refined lakeside retreat where comfort, design, and location come together beautifully.

206 Quayside Circle Unit 103, Maitland
$650,000
4 Beds ⋅ 2 Baths ⋅ Dommerich Hills Second Add SubDv. ⋅ 32751 Zip Code
***Charming Dommerich Hills Home with Scenic Lake Views and Modern Updates*** Nestled in the desirable Dommerich Hills, this beautiful 4-bedroom, 2-bath lakeside home offers a serene lifestyle with views of the lush conservation area and Lake Waumpi. Mature trees and an expansive backyard create a peaceful retreat, with ample space to add a pool. The home’s classic Florida charm is enhanced with modern features, including new double-paned, Low-E windows and doors for energy efficiency and comfort. Inside, the home showcases a blend of hardwood and porcelain tile floors throughout, providing an elegant and low-maintenance living space. The updated kitchen boasts stainless steel appliances, granite countertops, and a reverse osmosis system for the purest drinking water. A large office provides additional versatility, perfect as a guest room or a second living space. Recent upgrades include a new roof in 2022, a new AC unit installed in 2021, and a screened porch addition from 2019 that offers a perfect spot to enjoy the outdoors. Located within the sought-after Winter Park School District and already converted to the city sewer system, this home is move-in ready for its new owners. Don’t miss the opportunity to experience the best of Dommerich Hills – schedule your showing today!

2338 Tuscarora Trail, Maitland
$475,000
2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Take advantage of a rare opportunity to own one of only five double units at Lake Maitland Terrace, perfectly situated on the Winter Park chain of lakes. This 1,224-square-foot ground-floor residence offers 2 bedrooms and 2 baths and has been fully reimagined and renovated with designer finishes, luxury appointments, and thoughtful accessibility features, creating a home that effortlessly blends elegance, comfort, and modern convenience. Bright and inviting, this one-of-a-kind unit features custom cabinetry and lighting, shiplap walls, tongue-and-groove ceilings, wood-grain ceramic tile flooring, and bespoke window treatments throughout. The primary suite includes an ensuite bathroom with a roll-in shower and floating vanity. The gourmet eat-in kitchen comfortably seats eight and boasts a walk-in pantry and built-in appliances. Prewired for Smart-Home technology, this home allows for effortless voice activated control of the AC, lighting, TV, music, and front door locks. A dedicated laundry area completes the thoughtful design. Owners will also enjoy a front patio, accessible parking, and the convenience of walking to Lake Lily, the Enzian Theater, nearby shops and restaurants, as well as direct access to the lakes. This is a rare opportunity to own a fully renovated, one-of-a-kind residence that combines style, sophistication, and independence. Call today to schedule your showing.

1140 S Orlando Avenue Unit C2, Maitland
$815,000
4 Beds ⋅ 3 Baths ⋅ Lakewood Shores 1st Add SubDv. ⋅ 32751 Zip Code
Welcome to 185 Birchwood Drive, a rare Maitland SKIABLE LAKEFRONT retreat offering the perfect combination of privacy, elevation, and effortless Florida luxury. Positioned high above the waterline with sweeping lake views, this property delivers true lake living without the typical flood insurance requirement. Inside, the home is bright and inviting with luxury vinyl plank flooring throughout and a functional layout designed for both everyday comfort and entertaining. The open-concept main living space is highlighted by vaulted ceilings and a dramatic wall of glass framing the water, flowing seamlessly into the kitchen with generous cabinetry, stainless appliances, and a large center island ideal for gathering. The home also features beautifully updated bathrooms, and a split floor plan that provides ideal separation for guests, a home office, or multi-generational living. Outdoors, enjoy a private waterfront oasis complete with a resort-style pool, expansive entertaining space, and fully fenced yard perfect for dogs, and a updated 2019 roof. And because the lake is private, you can enjoy boating without the hassle of registering your boat—a rare convenience for waterfront owners. Perfectly located near I-4 with express lane access, 17-92, and just minutes to Park Avenue / Winter Park, this home offers the lifestyle buyers want most: stunning views, privacy, convenience, and true lakefront enjoyment.

185 Birchwood Drive, Maitland
$735,000
3 Beds ⋅ 3 Baths ⋅ Minnehaha Shores SubDv. ⋅ 32751 Zip Code
RARE opportunity to own a Maitland Shores home offering access to Lake Minnehaha AND the Winter Park Chain of Lakes. Residents enjoy exclusive use of the HOA lakefront park with a fishing dock and paved boat ramp that creates quick access to the Nina Canal and Lake Maitland — the largest lake in the Winter Park Chain. The unique location of this home offers an oversized .34-acre homesite that is thoughtfully landscaped with rare tropical plants, rose gardens, and a peaceful front courtyard complete with a bubbling fountain. Ample driveway and garage space accommodate boat or vehicle storage, ideal for enjoying skiable Lake Minnehaha. Inside, this 3 bedroom, 2.5 bath home offers 2,249 square feet of living space in a split floorplan. A unique highlight of the floorplan is the dual primary suites, each with private access to the screened pool, making the home ideal for multi-generational living. Equally beautiful pool views are also visible from the kitchen, breakfast nook, and spacious family room. If you are staying inside, the family room features a large fireplace that creates a cozy focal point. Just off the family room is the remodeled kitchen that is both bright and functional with abundant cabinetry, granite counters, stainless steel appliances, breakfast bar seating, a built-in desk, and a breakfast nook with patio access. Beauty abounds from the patio with a resort-style screened pool, complete with decorative palms surrounding the pool. Steps from the pool begin the meandering gardens with colorful blooms. To aid the avid gardener is a covered and secure garden shed. With such an expansive homesite - more than 15,000 square feet - possibilities for adding a full workshop or even an Accessory Dwelling Unit/ADU could be explored. Adjacent to this estate is Minnehaha Park, a 7.5-acre City of Maitland park offering multiple tennis courts, pickleball courts, walking trails, picnic pavilions, and playgrounds. While the setting of this property is quiet and serene, the home is minutes from Winter Park shopping and dining; downtown Maitland and Maitland City Centre; I-4 access; and zoned Winter Park High School. Additional home updates include a full roof replacement and AC replacement in 2021, making move-in and insurance smooth and easy. Don't miss this chance to get Winter Park Chain of Lakes access for yourself at this exceptional price!

109 Minnehaha Circle, Maitland
$1,199,500
5 Beds ⋅ 4 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code
Welcome home to one of the best-kept Maitland secrets, the neighborhood of Wellington. This lakefront home enjoys over 125 feet of linear frontage on Lake of Woods, a spring-fed skiable lake. Home is nearly 3,200 square feet, four bedrooms, three baths with incredible sunset views. Home is spacious with a first-floor primary suite and other bedrooms upstairs with generous flex space. Living space features a wood-burning fireplace with a vaulted ceiling and wood beam architectural accents. Two separate covered porches and screened pool make entertaining a breeze. Other features include solar power energy system (paid in full), newer roof, 2024 air conditioner, updated Hardie board siding, new windows, leaf guard gutter system, replumbed and more. This location is pristine close to many amenities and major roadways. This is a unique opportunity to enjoy lake life at its best.

1232 Wellington Terrace, Maitland
$749,900
2 Beds ⋅ 2 Baths ⋅ West Cove SubDv. ⋅ 32751 Zip Code
LAKEFRONT - Enjoy condo living at its finest from the top-floor Lake Maitland penthouse with million-dollar water and above treetop views, and beautiful panoramic sunrises from multiple rooms. This 9th-floor, 1,685 SF residence features 2 bedrooms, 2 baths, 2 multi-purpose rooms, and an open-concept kitchen, dining, and living area. Centered on the west cove of Lake Maitland, the largest of the Winter Park Chain of Lakes. The primary suite offers a spacious bath with an oversized walk-in shower and walk-in closet. The second bedroom includes guest bath access and a 6-ft soaking tub. Interior features include engineered wood flooring, plantation shutters, grand crown molding, and custom built-ins, display areas and doors. Three sets of French doors open to two balconies overlooking the lake. Balcony features electric hurricane shutters and a private 6’x5’ storage closet. A place of serenity, peace and beauty; with an energy of quiet, expansiveness and closeness to nature. Community amenities include resort-style pool and spa, boat docks, kayak racks, fitness center, clubhouse, and on-site management. Walk to Enzian Theater, Lake Lily Park, community center, library, dining, farmers market; minutes to Park Ave, Whole Foods, Winter Park Village, and major roads.

1100 S Orlando Avenue Unit 956, Maitland
$630,000
4 Beds ⋅ 3 Baths ⋅ Druid Isle SubDv. ⋅ 32751 Zip Code
Nestled in the highly desirable Druid Isle neighborhood, this single-family residence offers the perfect blend of comfort, style, and waterfront living. Boasting 2,162 square feet of thoughtfully designed living space, this 4-bedroom, 3-bathroom home is ideal for both everyday living and entertaining. A welcoming layout and abundant natural light create a warm, inviting atmosphere throughout. Step outside to your own private oasis, where a sparkling pool overlooks serene lakefront views, providing a picturesque backdrop for relaxation and outdoor gatherings. Whether enjoying morning coffee by the water or hosting sunset get-togethers, the outdoor space is designed to make the most of Florida living. The peaceful lake setting adds a sense of privacy and tranquility rarely found so close to it all. Completing the home is a spacious 2-car garage and a prime location in one of the area’s most sought-after neighborhoods. Druid Isle is known for its charm, convenience, and strong sense of community, making this property an exceptional opportunity. This lakefront pool home truly offers the lifestyle you’ve been looking for—comfort, beauty, and an unbeatable location.

1301 Druid Isle Road, Maitland
$897,000
4 Beds ⋅ 2 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
LOCATION! LOCATION! LOCATION! SERENE HOME in beautiful Dommerich Woods. Located on a quiet cul-de-sac, this unique .28+ acre property offers a single story, 4 bedroom + flex room split plan surrounded by peaceful nature. Brick driveway invites you to a gated courtyard leading to front door & fenced property offering complete privacy including pool, tranquil haven overlooking lush preserve & side yards for garden/play. Step inside to experience spacious foyer & living room with wood burning fireplace & wall of windows to front courtyard. The primary suite boasts a flex room perfect for home gym, office or nursery leading to 21x 14 primary bedroom!! Bright kitchen overlooks sparkling pool & family room leading to additional three bedrooms & guest/pool bath. This delightful home offers so much natural light, great closet space, hardwood floors, 2 car garage, new roof, gutters, AC, ductwork 2018, NO HOA!, Dommerich Elementary, Maitland Middle & Winter Park High & access to boat ramp on Lake Minnehaha leading to the Winter Park Chain of Lakes. WELCOME HOME!

821 Woods Court, Maitland
$3,000,000
Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code
A rare opportunity to secure a Lake Maitland homesite on the desired Maitland–Winter Park Chain of Lakes, an increasingly limited offering as quality lakefront parcels continue to disappear. Along a quiet street with an exceptional sense of privacy, this property lends itself beautifully to a gated approach and captures expansive southern-facing water views, offering breathtaking light throughout the day, from early morning glow to sunset skies. With approximately 27,472 square feet of uplands, the site has been cleared and is poised for new construction. Preliminary estimates suggest the potential for a residence in the approximately 10,000-square-foot range (approximately 40% of the lot size), though all building parameters should be verified through the City of Maitland and your architect/builder during due diligence. Existing improvements include a seawall plus a covered boat lift and dock, delivering immediate enjoyment of the Chain-of-Lakes lifestyle with boating, fishing and watersports right from your backyard. Envision a multi-generational estate designed for life on the water including morning paddle rides, afternoons on the dock and evenings spent poolside watching boats drift by. From here, it’s easy to embrace the local lake culture, whether cruising across the water or heading into Winter Park for boutiques, dining and energy of Park Avenue, while enjoying convenient access to downtown Maitland amenities and major roadways. Additional opportunity of the neighboring lakefront parcel at 125 Whitecaps Circle (approximately 18,500 square feet/.42 acres) is also available, presenting an exceptional option to combine two side-by-side properties for a larger estate footprint or a shared family-and-friends compound. All measurements and development assumptions are provided as estimates and must be confirmed by appropriate governing authorities and your design/construction team.

127 Whitecaps Circle, Maitland
$315,000
3 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code
Wake up to water views, an abundance of natural light, and tropical serenity in this beautifully appointed, private ground-floor residence. Embrace a calm, relaxing lifestyle in this light-filled, ground-floor condo surrounded by lush tropical landscaping, located in Maitland’s popular gated community of Sun Bay Club. Designed for effortless living, this spacious 3-bedroom, 2-bath residence offers a rare no-stairs layout and exceptional privacy, set on a desirable lot with no direct rear neighbors and tranquil pond views both behind and to the side. The elegant living area is anchored by a wood-burning fireplace, and flows through French doors into a sunlit, enclosed Florida room, with expansive windows and sliding glass doors—perfect for morning coffee, evening relaxation, or entertaining while enjoying serene, tropical surroundings. Sliding glass doors in the primary bedroom and kitchen open directly to the Florida room, enhancing the indoor-outdoor lifestyle. The kitchen features beautiful quartz countertops, stainless steel appliances, and a charming breakfast nook overlooking the pond, creating an inviting space to start each day. The second bedroom opens to a private patio with peaceful water views, while the third bedroom faces the front and offers flexibility as a home office, playroom, or guest retreat. LVP and ceramic tile flooring, abundant storage, and a thoughtfully designed layout provide both comfort and sophistication. Meticulously maintained with evident pride of ownership throughout. Recent upgrades include a newer A/C (2022) and a brand-new hot water heater (2025), newly painted areas interior. Enjoy the ease of walking to the community pool, lakes, and tennis courts, while coming home to a quiet, private setting. Centrally located just minutes from I-4, Winter Park, the beaches, the parks, hotels, dining, and shopping. Call today for your showing appointment!

1000 Winderley Place Unit 142, Maitland
$952,000
4 Beds ⋅ 3 Baths ⋅ Maitland Shores SubDv. ⋅ 32751 Zip Code
Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths. Step inside to discover hardwood floors flowing throughout the first level, leading to a dramatic sunken living room and formal dining room perfect for entertaining. The heart of the home is the spectacular family room featuring soaring 17-foot ceilings, a wood-burning fireplace, and expansive windows that bathe the space in natural light. The well-appointed kitchen boasts granite countertops, a charming breakfast nook, and glass sliders opening to a covered side porch—ideal for morning coffee or evening relaxation. The main level also includes a convenient guest bedroom and full bath, separate living and dining rooms, plus an attached 2-car garage. Upstairs, retreat to the loft-style primary suite with private en suite bath, two additional guest bedrooms, a hall bath, and laundry facilities for ultimate convenience. Outdoor living shines here with a front deck off the family room and multiple porch spaces. The quiet, dead-end street ensures peace and privacy. For just $100/year, the optional HOA provides deeded park access to beautiful Lake Maitland directly across the street—feel the refreshing lake breeze from your front door! Just minutes from the Winter Park Racquet Club and all that downtown Winter Park and Maitland have to offer. Zoned for award-winning Dommerich Elementary, Maitland Middle, and Winter Park High School. Complete with Terminix termite bond for peace of mind. This tranquil neighborhood retreat offers a rare combination of custom quality, natural beauty, and an unbeatable location. Don't miss this exceptional opportunity!

67 Cypress Lane, Maitland
$1,025,000
4 Beds ⋅ 4 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code
On a quiet street in one of Maitland's desirable neighborhoods, this home blends timeless elegance with modern comfort. This stunning residence offers a combination of sophistication and functionality, making it the ideal place to call home. Boasting four bedrooms, 3.5 baths and plenty of flex space, this residence spans over 2,600 square feet and sits on a generous .33-acre lot. Natural light draws you into the entry with views of the backyard oasis. The abundance of outdoor living that includes a covered porch with vaulted ceilings, private pool, two separate sitting areas with composite decking and garden areas, provide the backdrop for hosting family and friends. The kitchen is outfitted with stainless appliances (2025), ample cabinetry, a large walk-in pantry and granite/butcher block countertops. This split plan offers three bedrooms and two baths on the second level, one bedroom is complete with an en-suite bath. The peaceful owner's retreat is on the lower ground floor and is completely private from the rest of the living areas. It features a flex space/office as you enter the primary bedroom with a set of solid double doors. Once inside, you will notice two walk-in closets, an en-suite bath with a jacuzzi tub and separate shower, along with a walkout to a private courtyard area. Updates include roof in 2025, exterior paint in 2025, new wood fence in 2024, one HVAC in 2024 and solid wood doors with Baldwin hardware. Other features of the home include optional access to the Lake Minnehaha boat ramp, which leads to the exclusive Chain of Lakes. With easy access to downtown Maitland, Interstate 4, Maitland Community Park, Dommerich Elementary and Maitland Middle Schools, this home is a must-see!

798 Sequoia Trail, Maitland
$1,165,000
5 Beds ⋅ 3 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code
Built in 2014 and set within the highly sought-after Dommerich Estates neighborhood of Maitland, this thoughtfully maintained two-story home offers a rare blend of space, function, and location. With five bedrooms, three full bathrooms, and a flexible bonus room, the layout is designed to adapt easily to modern living. The entry opens to a formal dining space, while an additional room just off the foyer provides an ideal spot for a home office, den, or reading lounge. Dark hardwood floors anchor the main living areas and create a warm, cohesive feel throughout. At the heart of the home, the open kitchen and family room flow seamlessly together and look out over the backyard—perfect for both relaxed evenings and hosting gatherings. The kitchen features Bosch stainless steel appliances, granite countertops, a generous island with seating, and custom maple cabinetry, offering both style and practicality. The primary suite is privately positioned on the main level and includes two walk-in closets. Its en-suite bath is finished with double vanities, a soaking tub, a separate shower, and ceramic tile throughout. Two additional bedrooms on the first floor share a full bathroom with ceramic tile and a granite-topped vanity. Upstairs, a spacious bonus room creates endless possibilities, accompanied by two more bedrooms connected by a Jack-and-Jill bathroom with matching granite and tile finishes. Notable extras include an interior laundry room with washer and dryer, dual HVAC systems, and a fully fenced backyard with a lovely patio and plenty of room to add a pool or play area. Ideally located just moments from the new boardwalk leading to Maitland Community Park, residents enjoy easy access to walking paths, green space, playgrounds, and nearby tennis courts, enhancing the neighborhood’s active and outdoor lifestyle. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, the home also grants access to Lake Minnehaha, where residents enjoy a private boat ramp and fishing dock. A standout opportunity in one of Maitland’s most established and beloved lakefront communities. This home is back on the market after the previous buyer experienced a personal change in plans. No issues with the property.

1750 Cheyenne Trail, Maitland
$4,999,000
5 Beds ⋅ 8 Baths ⋅ Floridahaven SubDv. ⋅ 32751 Zip Code
Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.

360 Lake Seminary Circle, Maitland
$625,000
4 Beds ⋅ 3 Baths ⋅ Minnehaha Shores SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully refined 4-bedroom, 3-bath POOL HOME in the highly sought-after Minnehaha Shores community of Maitland. Situated on a prominent corner lot with picturesque views of Minnehaha Park, this residence offers thoughtful enhancements, generous indoor–outdoor living, and exclusive neighborhood lake access to the Winter Park Chain of Lakes. Step inside to an airy, open layout filled with natural light, complemented by luxury vinyl plank flooring and plantation shutters throughout. The chef’s kitchen is the heart of the home, featuring granite countertops, subway tile backsplash, butcher-block accents, premium stainless steel appliances, and abundant cabinetry. The kitchen flows seamlessly into the dining and family rooms, ideal for daily living or effortless entertaining. A separate formal living room with pocket doors provides flexible space for work, relaxation, or hosting guests. Four well-appointed bedrooms provide comfort and versatility, including a spacious primary suite with a thoughtfully designed ensuite bath. The fourth bedroom can serve as a home office, guest room, or creative space. A rare dedicated pool bath adds convenience, and all bathrooms showcase modern tile work and stylish finishes. An indoor laundry/utility room enhances day-to-day functionality. Step outdoors to a quintessential Florida oasis with a sparkling private pool, expansive patio, and fully fenced green space, perfect for entertaining, quiet mornings, or recreation. Major improvements completed in 2013 include enhanced electrical and HVAC systems, providing peace of mind and long-term ease. Located at 10 Minnehaha Cir, Maitland, FL 32751, this home rests on a tranquil cul-de-sac surrounded by beautifully maintained homes and a friendly neighborhood atmosphere. Residents enjoy private lake access, a community boat ramp, and a dock—amenities rarely found at this price point. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, this location is among Central Florida’s most desirable. More than move-in ready, this home blends timeless character with modern comfort in one of Maitland’s premier neighborhoods. Every room has a story, every space invites possibility, and each day feels like the start of something special. The best journeys always lead home—and this one begins here.

10 Minnehaha Circle, Maitland
$243,000
3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs Ph 02 SubDv. ⋅ 32751 Zip Code
Experience lakeside living in this elegant 3-bed, 3-bath townhome in the heart of Maitland! This 1,575 sq ft residence offers refined, comfortable living with tranquil lake views. The townhome features two upstairs ensuite bedrooms—one with a private balcony overlooking the lake, a perfect spot to enjoy your morning coffee—and a convenient first-floor bedroom that provides space and ease. Enjoy a large patio ideal for entertaining, plus community amenities including a pool and park. Prime Maitland location near Maitland City Centre, SunRail, I-4, and upscale dining and shops. Currently leased through 2/2026, this serene lakeside townhome offers the rare flexibility of a strong investment today and a sophisticated primary home tomorrow. Experience the beauty and convenience of Maitland living—book your private tour today!

806 Town Circle Unit 156, Maitland
$415,000
3 Beds ⋅ 2 Baths ⋅ Lake Eulalia Heights SubDv. ⋅ 32751 Zip Code
Step into timeless style with this completely updated mid-century modern home tucked away on a quiet Maitland cul-de-sac. This 3-bedroom, 2-bath residence offers 1,521 sq ft of thoughtfully designed living space featuring refinished terrazzo floors, brand-new windows, and abundant natural light. The modern kitchen shines with new cabinets, stone countertops, and stainless-steel appliances, while both bathrooms have been beautifully remodeled with contemporary finishes. Fresh interior and exterior paint, new lighting and ceiling fans throughout, and lush new landscaping make this home truly move-in ready. Enjoy the best of Central Florida living—just steps from Maitland’s shops and restaurants and minutes from charming downtown Winter Park

6 Barnard Court, Maitland
$571,000
3 Beds ⋅ 4 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
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1240 Trust Lane, Maitland
$159,000
2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Welcome to Lake Maitland Terrace, a charming lakeside community of Mid-Century Miami Modern condos set within eleven cottage-style buildings along the shores of Lake Maitland. Residents enjoy resort-style amenities, including a recently renovated lakeside pool, fishing dock, putting green, shuffleboard courts, and a clubhouse with kitchen. This first-floor, two-bedroom, one-bath condo in the Arlington Building has been maintained by the same owner for nearly 30 years. Updates include a 2021 AC, 4-year-old water heater, newer windows and front door, and a new roof (2023–2024). The open great room flows into the dining area, and the adjacent kitchen features a 2nd entrance. Much of the interior remains in original condition, and the old carpet has been removed, providing an ideal opportunity for a new owner to update and make it their own.  Additional features include one designated parking space, ample guest parking, enclosed bicycle storage, convenient laundry facilities, and racks for kayaks and paddleboards. The location is unbeatable—walk to the Enzian Theater and Lake Lily, or drive just five minutes to downtown Winter Park with easy access to I-4. Condo is being sold AS IS.

1140 S Orlando Avenue Unit A5, Maitland
$540,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code
Welcome to The Moorings, a rarely available lakeside community perfectly positioned across from beautiful Lake Lily. This fully renovated 4th-floor condo combines modern elegance with stunning water views of Lake Maitland, visible right from your living room and screened-in balcony. Inside, you’ll find an open, light-filled layout with white-oak luxury vinyl flooring that sets a clean, contemporary tone. The kitchen has been completely updated with premium appliances, quartz countertops, and brass fixtures, creating a space that’s both stylish and functional. The primary bedroom suite features a spacious walk-in closet and a beautifully finished en-suite bathroom with a large walk-in shower. A second bedroom and full bath offer plenty of room for guests or a home office. Additional conveniences include an in-unit laundry room with washer and dryer, plus elevator access for easy entry. Residents of The Moorings enjoy a host of amenities, including a sparkling community pool, private boat docks, a scenic pier with seating area, a fitness center, and a clubhouse for gatherings. Located just minutes from top-rated restaurants, shopping, and entertainment in Maitland and Winter Park, this condo offers the ideal blend of tranquility and city convenience. Come experience lakefront living at its finest.

206 Quayside Circle Unit 404, Maitland
$1,425,000
3 Beds ⋅ 3 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code
Sophisticated and timeless, this stunning one-story home was completely reimagined in 2019 by multi-award-winning builder and design through Z-Properties. Taken down to the studs and rebuilt with the finest materials, this split-plan three-bedroom, three-bath residence blends modern design with an inviting, incredible design feel. Gorgeous high grade wood flooring throughout along with expansive windows and walls of glass flood the interiors with natural light, taking advantage of picturesque views! The backyard is a sanctuary setting with Signature Landscape mature landscaping and sparkling pool and separate spa. The open concept design is ideal for daily living and entertaining, with a seamless flow extremely well thought-out living areas. A designer-inspired gas fireplace in the dining area creates a sophisticated and welcoming ambiance, while two sets of glass doors in the living room open to the inviting outdoor living spaces. The stately kitchen is a showpiece, featuring Thermador Pro Series appliances, a Sub-Zero wine tower, and elegant counters that elevate form and function. The primary suite offers a private retreat with a generous walk-in closet and a spa like well-appointed bath. Two additional bedroom suites are equally refined, each with custom closets for optimal storage and organization. Outside, every detail has been thoughtfully curated. The private front courtyard, centered around a tranquil Zen fountain private courtyard, sets the tone for the home's refined elegance. The rear outdoor living area features Brazilian IPE wood decking surrounding the heated saltwater pool, alongside lush landscaping, complete with sculpted hedges and tropical palms, creates a resort-like ambiance. A built-in summer kitchen includes a gas grill and green egg off the kitchen, and flex space is framed by a beautiful bougainvillea hedge for added serenity, ideal for effortless outdoor entertaining. Lastly there is a fully finished garage with indoor/outdoor carpeting and is temperature controlled with its mini-split AC unit. Residents of Hollieanna Shores enjoy deeded lake access to Lake Maitland, part of the prestigious Winter Park Chain-of-Lakes, via a private community boat ramp. Ideally with convenient access to major roadways, this exceptional home offers easy commutes to downtown Winter Park, Orlando and area airports, a sophisticated retreat in one of Central Florida's desirable Maitland/Winter Park hidden gem neighborhoods!

123 Hollie Court, Maitland
$850,000
2 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 05 SubDv. ⋅ 32751 Zip Code
Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water.

219 Quayside Circle, Maitland