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$455,500
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
This property is currently under contract.

1317 Medinah Court, Winter Park
$660,000
4 Beds ⋅ 2 Baths ⋅ Williamsburg SubDv. ⋅ 32792 Zip Code
Welcome to this well-maintained Winter Park home, proudly cared for by its original owner. With a BRAND NEW ROOF and BRAND NEW AC system, this property combines peace of mind with long-term value. Set on a spacious quarter-acre lot with NO HOA, it offers flexibility, privacy, and convenience in one of Central Florida’s most desirable locations. This home features a durable roof with a 10-year transferable warranty, engineered to withstand winds of up to 130 mph for lasting protection and peace of mind. Step inside through the front entry into a light-filled formal living room, where large windows set a warm and welcoming tone. Just to the right, the formal dining room provides the perfect space for family gatherings or entertaining. Flowing naturally into the main family room, you’ll find a cozy fireplace that anchors the space and creates an inviting setting for everyday living. The kitchen is designed for function with all appliances included, ample counter space, and a thoughtful connection to the laundry room, which features generous storage and everyday convenience. Off the family room, the Florida room is bright and versatile—ideal for a home office, reading nook, or playroom. One of the standout features is the expansive 483 sq. ft. bonus room, offering endless possibilities as a game room, studio, or additional living space to suit your lifestyle. Outdoors, a screened-in porch overlooks the fenced backyard, providing a comfortable spot to relax, garden, or host gatherings. An included shed adds extra storage for tools and equipment. Each bedroom is well-sized, offering comfort and practicality, with bathrooms that have been cared for and maintained with attention to detail. The thoughtful layout balances privacy and community spaces, making it both functional and inviting. Location is key, and this home delivers. Just a few minutes’ walk takes you to the scenic Cady Way Trail, Winter Park Pines Golf Course, and Winter Park High School. Nearby parks, shopping, dining, and top-rated schools add to the convenience, while downtown Winter Park, Orlando attractions, and major highways are only a short drive away. Perfect for buyers seeking a primary residence, an Orlando relocation home, or a smart Central Florida real estate investment, this property is a rare find. With only one owner since construction and NEW major systems in place, this Winter Park gem is ready for its next chapter. Contact us today for a private tour or more details on this exceptional opportunity.

2421 Summerfield Road, Winter Park
$335,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 09 SubDv. ⋅ 32792 Zip Code
Are you looking for a great house set on an incredible piece of land? Well look no further because this house sits in the subdivision Eastbrook. This split floorplan has a large open kitchen with a large area for eating breakfast and a separate dining room. The master boasts of a walk in closet and an remodeled master bath. While this house still has a lot of it's original charm, it has been loving maintained and you would make home owner number 3! The main bathroom has an a completely remodeled shower and easily accessible for any age! The size of the lot of yard has endless potential whether you want to add a pool, playground or even an additional room it is up to you! Oh and the AC unit is from 2020 and the hot water heater is new too! This property is as is/where is.

3525 Baxter Drive, Winter Park
$199,000
2 Beds ⋅ 2 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code
One of the lowest-priced homes in Winter Park with nearly 1,400 square feet, a private carport, screened balcony, community pool, and easy access to UCF, Full Sail, Rollins, Valencia East, Orlando International Airport, and downtown Orlando! The monthly HOA covers many exterior maintenance items so you can enjoy low-maintenance living.This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!

7471 Canford Court Unit 19, Winter Park
$345,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Welcome to your slice of Winter Park paradise! Nestled in the sought-after neighborhood of Winter Park Estates, this 3-bedroom, 2-bath home sits on a quarter-acre lot surrounded by mature landscaping and Florida sunshine. Inside, natural light pours through the windows, highlighting spacious living areas and an inviting Florida room that overlooks the sparkling pool—perfect for relaxing or entertaining. The two-car garage includes a workbench area, ideal for projects or extra storage. Whether you’re dreaming of updating, expanding, or simply enjoying the Florida lifestyle as-is, this home offers a blank canvas for whatever your heart desires. Zoned for top-rated schools and located just minutes from the best of Winter Park dining, shopping, and parks—this is an opportunity you won’t want to miss.

731 Bongart Road, Winter Park
$899,000
4 Beds ⋅ 3 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Discover elevated living in this stunning 4 bedroom, 2.5 bathroom pool home, perfectly situated overlooking a tranquil pond and Winter Park 18 hole golf course. Surrounded by a lush tropical backyard oasis, this residence blends modern sophistication with effortless comfort, creating a serene retreat that’s ideal for that perfect start to the morning with a cup of coffee or a relaxing wind down at sunset with a glass of wine. Inside, vaulted wood-trimmed ceilings and a wood-burning fireplace set a warm, inviting tone across 2,455 sq. ft. of thoughtfully designed space. The kitchen features contemporary cabinetry paired with quartz and butcher block wood countertops and a designer tile backsplash. Stainless steel appliances, including a beverage refrigerator, add a professional touch, while a built-in banquette provides seating for six—perfect for entertaining and everyday living. The primary suite offers wood floors, a walk-in closet, and a spa-like bath with dual floating vanity, soaking tub, and seamless glass shower. Enjoy outdoor living at its finest with pergola-covered sitting areas, outdoor shower, fire pit, and sparkling pool. Situated on a private tree-lined cul-de-sac, this home is located in a prime location just minutes from Cady Way Trail, Cady Way pool & courts, Winter Park Pines Golf Course, Crosby Center for Health and Wellbeing, Ward Park, Showalter Athletic Complex, Advent Health Winter Park Hospital and less than 10 minutes to Historic Park Avenue fine dining and shopping. Don’t miss your chance to own this rare Winter Park gem—schedule your showing today! ROOF - 2016 HVAC - 2023(2) PLUMBING - 2020 ELECTRICAL - 2021 WATER HEATER - 2020

1648 Cypress Point Lane, Winter Park
$398,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome to 3529 Australian Circle, a beautifully updated 3-bedroom, 2-bathroom POOL home located in the desirable EASTBROOK subdivision of WINTER PARK. Designed for comfort and everyday living, this home blends modern updates with timeless character. Step inside to find an open floor plan enhanced by high ceilings, WOOD-LOOK TILE flooring in the main living areas, and BAMBOO flooring in all three bedrooms. The REMODELED kitchen (2022) serves as the heart of the home, featuring BUTCHER BLOCK countertops, timeless cabinetry with soft-close drawers, a large breakfast bar, and a new mini-split system for improved air circulation. The kitchen flows seamlessly into the dining area and great room, creating a welcoming space for both entertaining and everyday moments. Adding warmth and character, the shiplap ceilings in the kitchen and great room tie the design together. The interior was freshly PAINTED in 2023, while crown molding (2024) adds a refined finishing touch. Step through the French doors into your private backyard oasis—complete with a covered porch featuring a tongue-and-groove ceiling, a fully FENCED yard, and a large open-air pool accented with flagstone. The 2023 irrigation system keeps the beautiful exotic palms thriving, and the system draws from a backyard aquifer, helping to save on water bills. The primary suite offers a peaceful retreat with an en-suite bathroom, granite countertop, and a walk-in shower with travertine tile. Two additional bedrooms share a stylish second bathroom. Practical updates provide peace of mind, including a roof (2018), A/C (2018), electrical panel (2021), water heater (2022), and double-paned windows. The SIDE-ENTRY one-car GARAGE adds convenience and curb appeal. Take advantage of an Exclusive Offer: 1% of loan amount toward closing costs or rate buy-down. Inquire today! Located on a quiet street with no HOA restrictions, this home is zoned for top-rated Seminole County schools and just minutes from Park Avenue’s shopping and dining, Rollins College, Winter Park Hospital, and nearby museums. With its thoughtful updates, inviting layout, and unbeatable location, this home offers an exceptional opportunity to enjoy the Winter Park lifestyle. Schedule your private tour today!

3529 Australian Circle, Winter Park
$206,000
1 Beds ⋅ 1 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code
Welcome to this charming and spacious 1-bedroom, 1-bathroom home featuring an open-concept layout filled with natural light. Each area is equipped with its own independent air-conditioning unit for maximum comfort. The modern kitchen is perfect for everyday living and entertaining guests. The property is fully fenced, offering privacy and security, and includes a large backyard ideal for outdoor enjoyment. An outdoor laundry area with a washer and dryer is conveniently included for your comfort. Additionally, there is an optional studio space, ideal for a home office, gym, or guest room. Perfectly located near restaurants, pharmacies, and local shops, this home provides easy access to everything you need for a comfortable and convenient lifestyle. Schedule your showing today and make this lovely home yours!

5206 Seminole Avenue, Winter Park
$500,000
4 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Winter Park “Love Shack No More” – 4 Bedrooms, 2 Baths, and Plenty of Potential! When they said “happily ever after,” they didn’t mention drywall dust and half-finished projects! This 4-bedroom, 2-bath home in highly sought-after Winter Park comes straight from a divorce split, which means one lucky buyer gets the rare chance to finish what love couldn’t — a home with solid bones and serious potential. Some renovations are already underway — think new finishes, updated spaces, and the kind of promise that makes HGTV jealous — while a few projects are still waiting for someone handy (or just brave) enough to see them through. Set on a quiet street close to top-rated schools, charming boutiques, and Winter Park’s favorite restaurants, this property is ideal for anyone who can look past a little sawdust and see the dream beneath. Whether you’re a renovator, a romantic, or just someone who loves a good comeback story, this is your chance to turn “it’s complicated” into “move-in ready.” Sold As-Is — because closure never looked so good.

2758 Sandwell Drive, Winter Park
$415,000
4 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
BACK ON THE MARKET AND PRICED BELOW MARKET IN DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! ALLOWS SHORT TERM RENTALS (STR). LOW TAX DISTRICT. This is probably the closet you can get to Winter Park (Park Ave) without having to pay the Winter Park taxes or conform to their restrictions! This property has been extremely well maintained and would be an amazing home for a new family. ROOF IS 2023! All systems have been updated or serviced. Property features include 4 BEDROOMS, 2 BATHROOMS, 1,725 TOTAL SQFT, ATTACHED IN-LAW SUITE WITH ITS' OWN ENTRY, HUGE BACK YARD WITH LOT SITTING ON APPROX. 10,000 SQFT, TILE THROUGHOUT, STAINLESS APPLIANCES INCLUDED, FENCED, AND MORE. Seller is willing to give $5,000 credit towards the buyer's closing costs or buying down their interest rate (inquire about conditions). *More than one of the photos has been virtually staged.

1816 Ivy Lane, Winter Park
$390,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 Rep Of Pt Of Blk 14 SubDv. ⋅ 32792 Zip Code
This stunning home has been completely renovated and is ready for you to move in! Featuring 3 bedrooms, 2 full bathrooms, and a screened-in pool with a spacious deck, it blends modern style with everyday comfort. Inside, you’ll find brand-new waterproof laminate flooring, fresh paint throughout, and stylish modern finishes that create a light and inviting atmosphere. The open and spacious common areas flow seamlessly, offering the perfect setting for gatherings and entertaining. The kitchen is equipped with stainless steel appliances, while both bathrooms have been fully remodeled with sleek, contemporary details.Enjoy Florida living outdoors with your private screened pool area, perfect for relaxing weekends or evening swims. Situated in a prime Winter Park location, you’ll be just minutes from major highways, Winter Park Village, shopping, dining, and local attractions. This home combines modern upgrades, a convenient location, and the perfect setting for enjoying the Florida lifestyle. Don’t miss your chance to own this move-in ready Winter Park gem!

1670 Clematis Lane, Winter Park
$935,000
Aloma SubDv. ⋅ 32792 Zip Code
This Winter Park investment opportunity is prime for Developers, Builders, & Investors for redevelopment. The Hawick Lane property is currently vacant as the home and trees were recently demo'ed. The future development of three (3) fee simple single family lots (50’ wide) is the highest and best use of this land. The lot split process is complete with individual surveys for each 50' wide lot. The total land area is approximately 19,698sf. (150ft street frontage by 140ft lot depth).

2260 Hawick Lane, Winter Park
$610,000
3 Beds ⋅ 2 Baths ⋅ No Subdivision SubDv. ⋅ 32792 Zip Code
Motivated Seller | Rare Live/Work Opportunity in Winter Park** Ideal for a true live/work setup, with potential for office, retail, daycare, studio, or other permitted uses (subject to zoning verification). Fully renovated property with two adjoining parcels, including a vacant lot (50' x 155') offering future expansion potential (subject to county approval). Situated on over half an acre with flexible commercial/residential zoning, this is a strong opportunity for an owner-user or investor seeking versatility and upside. Features include: 2-car garage, security system with cameras, reception area, 3 private offices, conference/living room, kitchen, 2 bathrooms (one convertible to full), and a dedicated studio space. Furnishings available. Currently set up as a recording studio/office. Owner financing possible. Potential uses (subject to verification) • Live/work residence • Residential or short-term rental potential • Professional or medical office • Service-based business with workspace • Retail, daycare, or educational use • Creative studio or content production Prime Location: • ~15 min to UCF, Full Sail & Downtown Winter Park • ~25 min to Downtown Orlando • Easy access to 417 & I-4

5150 Old Howell Branch Road, Winter Park
$440,000
5 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
Spacious 5-Bedroom Pool Home in Winter Park – Over 2,200 Sq Ft, Prime Location Near Interlachen Country Club Welcome to 5073 Lake Howell Road, a rare opportunity to own a 5-bedroom, 3-bath pool home with over 2,200 square feet of living space, set on a generous lot in the heart of Winter Park. Surrounded by million-dollar new construction homes and located just minutes from Interlachen Country Club, this property offers both immediate comfort and long-term investment potential in one of Central Florida’s most desirable areas. This single-story residence features a flexible layout designed to meet a variety of needs. Inside you’ll find multiple living and dining areas, a spacious kitchen with solid cabinetry and ample storage, and generously sized bedrooms perfect for family, guests, or home office space. With a roof replaced in 2021, one of the largest expenses of homeownership has already been taken care of, providing peace of mind as you move in or plan future updates. The home’s versatile floor plan offers endless potential. Whether you’re looking to renovate and modernize, add luxury finishes, or design a fully customized Winter Park dream home, this property delivers the space and structure to bring your vision to life. Step outside and enjoy Florida living at its best. The screened-in pool and covered patio provide the perfect space for entertaining, relaxing, or soaking up the year-round sunshine. The fenced backyard adds privacy and flexibility for pets, gardening, or outdoor recreation. Location is everything, and this home delivers. You’ll be just a short drive to Winter Park’s Park Avenue with its boutique shops, fine dining, and cultural attractions, while also being close to the Winter Park YMCA, top-rated schools, and major roadways. Centrally positioned, you’ll have convenient access to Maitland, Casselberry, and Altamonte Springs, making this property a perfect hub for work, play, and everyday living. With its combination of size, pool, newer roof, and prime setting in a gentrifying neighborhood, 5073 Lake Howell Road is ideal for investors, renovators, or homeowners seeking a long-term opportunity with instant upside. Don’t miss this rare chance to secure one of Winter Park’s most versatile and well-located homes. Schedule your private showing today and see the full potential of this property firsthand.

5073 Lake Howell Road, Winter Park
$450,000
4 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Available, making it an excellent opportunity for qualified Buyers. Welcome to 1422 Tierra Circle, beautifully refreshed immaculate pool home located in the well-established community of Casa Aloma, featuring 4 bedrooms, 2 full bathrooms and open floor plan. You will notice the enhanced curb appeal from the moment you arrive with newly painted exterior and driveway along with lush landscaping, creating a warm and inviting first impression. Many wonderful upgrades include a newer roof (2020), new electrical panel (2025), HVAC system (2022), HVAC/ air ducts cleaned and sanitized (2025), screened backyard patio (2023), new pavers and exterior shutters for added curb appeal, updated light fixtures, beautiful new front exterior door, new pool pump and luxury vinyl and carpet flooring (2022). The spacious living room flows into a versatile bonus area, both with excellent backyard pool views from the large window and sliding doors, allowing natural sunlight in. The bonus area is currently used as a playroom and ideal for an office space, library, bar or reading nook, leading to the kitchen. The kitchen is a chef’s delight, with stainless steel appliances, a gas stove and granite countertops, overlooking the dining room and sliding doors that open to the spacious screened patio and fenced backyard paradise. The large primary suite offers a peaceful retreat with double his-and-her closets and private ensuite bath, while three additional bedrooms provide flexibility for family, guests, or work-from-home needs. Step outside and enjoy true Florida living in your private backyard paradise, with a spacious screened patio, freshly painted pool deck, sparkling pool and an abundance of fruit trees, including limes, avocados, bananas, guavas, and mangos, perfect for entertaining or simply relaxing in the sunshine while enjoying fresh produce right at home. EXCELLENT LOCATION zoned for top-rated schools, minutes away from AdventHealth, Full Sail University, FL-436, and endless shopping and restaurants nearby. Come take a tour of this immaculate 4 bedrooms, 2 bathrooms immaculate pool home today!

1422 Tierra Circle, Winter Park
$330,000
4 Beds ⋅ 2 Baths ⋅ Springview SubDv. ⋅ 32792 Zip Code
Discover this spacious 4-bedroom, 2-bath BLOCK home situated on a generous QUARTER ACRE LOT lot with NO HOA—offering you the freedom to truly make it your own. Nestled in the heart of Seminole County, this home sits just minutes from Lake Howell High School, UCF, 417, and all the shopping and dining you could want. Inside, you'll find a bright and functional layout perfect for families, roommates, or first-time buyers looking for room to grow. The backyard offers space for a garden, pets, or future expansion—and with a NEW ROOF, the possibilities are endless. Zoned for TOP-RATED SEMINOLE COUNTY SCHOOLS and ideally located for commuters and students alike, this property is a rare opportunity in a rapidly growing area. Don’t miss your chance to put down roots in one of Central Florida’s most convenient and desirable neighborhoods. Schedule your private tour today!

3041 Dikewood Court, Winter Park
$430,000
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 01 SubDv. ⋅ 32792 Zip Code
This is your chance to own a rare updated 3-bedroom, 2-bath pool home in the heart of Winter Park. This move-in-ready property features luxury vinyl plank flooring, quartz countertops, GE Café appliances, and a gourmet induction oven. A dedicated laundry room and 1-car garage add additional convenience and comfort to this charming home. Recent updates include a 2023 roof, 2024 A/C, brand-new vinyl fence, resurfaced pool/tilework, and a newly added hot tub. Enjoy a private fenced backyard with plenty of space to relax or entertain, all within minutes of Park Avenue, Baldwin Park, and top Winter Park schools.

5122 N Woodcrest Drive, Winter Park
$130,000
1 Beds ⋅ 1 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to this inviting first-floor 1 bedroom, 1 bathroom condo with a private patio overlooking the sparkling community pool. Step inside to find a bright and open living space with easy access to outdoor relaxation—perfect for morning coffee or evening unwinding. The unbeatable location puts you in the center of it all—just minutes from Rollins College, UCF, and Full Sail University, with convenient access to shopping, dining, and movie theaters. Whether you’re a first-time homebuyer, student, investor, or looking to downsize, this condo offers both comfort and value in one of Central Florida’s most desirable areas. Community amenities include a pool, well-maintained grounds, and plenty of parking. With its prime Winter Park location and low-maintenance lifestyle, this home is a fantastic opportunity you don’t want to miss!

200 Saint Andrews Boulevard Unit 101, Winter Park
$470,000
5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 15 SubDv. ⋅ 32792 Zip Code
The pool home you’ve been waiting for is here! Welcome to this beautifully renovated 5-bedroom, 3-bathroom home offering 1,546 SF of living space, abundant natural light in every room, a spacious screened porch, a private pool, and a Mother-in-law Suite with its own private entrance—perfect for guests, multi-generational living, or rental income. The primary suite features a connected den, ideal for an office or nursery, and the spacious bedrooms provide plenty of flexibility. Upgrades include a remodeled kitchen (2024), remodeled bathrooms (2024), new floors (2024), re-plumbing (2024), new dishwasher (2025), updated electrical, and an A/C is 2010 and Water Heater replaced in 2020. Step outside to your private pool and expansive yard, complete with a new fence (2024), a new shed, and a pool pump replaced in 2023—creating the ultimate Florida retreat. Move-in ready and thoughtfully updated, this home seamlessly blends modern living, flexible indoor spaces, and resort-style outdoor amenities. Ideally located in the heart of Winter Park, with effortless access to shops, restaurants, top-rated schools, and major highways, and conveniently reachable from both Aloma Avenue and Howell Branch Road, this exceptional property won’t last long—schedule your private showing today and see it for yourself!

3319 Ellwood Court, Winter Park
$387,000
3 Beds ⋅ 3 Baths ⋅ Howell Branch Woods SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome home to 5422 Albert Drive this beautifully remodeled 3-bedroom, 2-bathroom home is located in the heart of Winter Park. Situated on a generous 0.21-acre lot with no HOA, this home offers the perfect blend of modern upgrades and everyday comfort in a highly sought-after location. Inside, you'll find brand-new wood-look tile flooring throughout—no carpet—offering both durability and style. The fully remodeled kitchen is a standout feature, showcasing a brand-new stainless steel appliance package, sleek finishes, and a functional layout that’s ideal for both entertaining and daily living. Both the primary and secondary bathrooms have been completely renovated with high-end touches, creating spa-like spaces you’ll love coming home to. Freshly painted inside and out, the home also features new lighting and ceiling fans throughout, giving each room a bright and inviting feel. Major updates include a new roof and new AC system installed in 2023, new windows for enhanced energy efficiency, and a new hot water heater added in 2025. The home has also been fully repiped and received a complete electrical update, providing peace of mind for years to come.This is a truly turnkey property offering move-in-ready convenience in a prime Winter Park location close to top-rated schools, shopping, dining, and parks. With no HOA, you’ll enjoy extra freedom and flexibility to make this home your own. Don’t miss the chance to own this stunning, like-new home in one of Central Florida’s most desirable communities. Schedule your private showing today!

5422 Albert Drive, Winter Park
$260,000
3 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Spacious End-Unit Condo in Prime Winter Park Location – Quiet Dead-End Street! Welcome to this well-maintained 3-bedroom, 2-bath end-unit condo offering 1,311 sq ft of comfortable living space in the heart of Winter Park. Situated on a quiet dead-end street, this desirable end unit provides extra privacy, added natural light, and a peaceful setting within a beautifully kept community. Step inside to an inviting open floor plan featuring a cozy family room with a wood-burning fireplace, perfect for relaxing evenings or entertaining guests. The space flows into a bright dining area and a well-maintained kitchen, while a private screened-in back porch extends your living area outdoors. The spacious primary suite includes an en-suite bath, and the two additional bedrooms offer flexibility for guests, family, or a home office. Enjoy a variety of community amenities including a sparkling pool, dog run, and two tennis courts, all within a quiet, friendly neighborhood setting. Located just minutes from Downtown Orlando, MCO Airport, Full Sail University, and Rollins College, this condo offers convenience, comfort, and great value in one of Central Florida’s most sought-after areas. Don’t miss your chance to see this charming home—schedule your private tour today!

2489 Tahoe Circle, Winter Park
$569,990
4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code
Welcome to your dream home in the heart of Winter Park! Nestled in a quiet and sought-after neighborhood, this beautifully maintained 4-bedroom, 2-bathroom pool home offers 1,889 square feet of comfortable living space and the perfect blend of privacy and convenience. Backing directly to the prestigious Interlachen Golf Course, you'll enjoy peaceful views with no rear neighbors — a rare find in such a prime location. Step inside to discover spacious living areas, an updated kitchen, and plenty of natural light throughout. The 2-car garage provides ample storage, while the home's layout offers both functionality and flow, making it ideal for everyday living and entertaining. Each of the four bedrooms is generously sized, and the two bathrooms are tastefully appointed, offering both style and comfort. Outside, the backyard is a true oasis. Lush, mature landscaping surrounds the sparkling pool, creating a serene and private retreat perfect for relaxing or hosting gatherings. Whether you're enjoying a morning coffee poolside or an evening under the stars, this outdoor space is a showstopper. All of this is just minutes from charming Park Avenue and vibrant downtown Winter Park, with shopping, dining, and entertainment right at your fingertips. Don’t miss this rare opportunity to own a slice of paradise in one of Central Florida’s most desirable communities! ROOF - 2020 AC - 2025

1561 Nottingham Drive, Winter Park
$395,000
3 Beds ⋅ 2 Baths ⋅ Georgetown Estates Ut 1 SubDv. ⋅ 32792 Zip Code
PRICE IMPROVEMENT, PRICED TO MOVE QUICK!! NEW AC 2019, NEW ROOF 2016, NEW SOLAR PANELS 2019!! 3.2% Assumable VA Eligable! This beautifully renovated 3-bedroom, 2-bathroom home combines modern upgrades, energy efficiency, and an unbeatable location. Step inside to a completely remodeled kitchen featuring dark hardwood cabinets, granite countertops, and stainless steel appliances. The open-concept design seamlessly connects the kitchen, dining, and living areas, creating the perfect space for entertaining. A large sliding glass door floods the home with natural light and opens to your private patio and sparkling pool deck. Throughout the main living areas, you’ll find stylish wood-look tile, with laminate flooring in the bedrooms for comfort. The fully fenced backyard is enhanced with mature landscaping, offering both privacy and charm. This home is packed with smart upgrades: Natural gas-powered A/C and water heater, with option to convert the range to gas. Upgraded windows, doors, and added insulation for efficiency. A full solar system under warranty, eliminating electricity bills! Home warranty included for added peace of mind on all major appliances. Located in the highly sought-after Winter Park High School zone, this property offers not only a beautifully upgraded home, but also the lifestyle and convenience of one of the best communities in Central Florida. Don’t miss this opportunity—move-in ready, energy-efficient, and ideally located!

3214 Lowndes Drive, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 1st Add SubDv. ⋅ 32792 Zip Code
Wait no more! Don’t miss this charming and hard to find 3 bed/ 2 bath PLUS bonus room in Brookshire Heights! Large treed lot walking distance to Brookshire Elementary, Showalter Field, Cady Way Pool and Park and the Advent Health Winter Park Complex. Ready for your personal touches, this well loved home has large living room and dining area, terrazzo floors, vintage cabinetry, great closets and storage, newer windows and roof! Patio and large shed in rear yard. Inside utility room, washer/dryer, single car garage with workshop. Seller will provide $5000 decor credit with an acceptable offer!

2485 Middleton Avenue, Winter Park
$515,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated and meticulously maintained home, nestled on a spacious corner lot in the highly sought-after Winter Park neighborhood—where the mailman still delivers right to your front door. Combining classic charm with modern upgrades, this three-bedroom, two-bathroom home offers the perfect balance of style, comfort, and functionality. Step inside to a bright and open layout featuring a formal living and dining area with gorgeous hardwood flooring, updated light fixtures, and ceiling fans throughout. An additional family room, bathed in natural light, creates a welcoming space to relax or entertain guests. The heart of the home is the stunning kitchen, completely remodeled in 2019. Designed with both beauty and function in mind, it features KraftMaid white shaker-style maple cabinetry, sleek quartz countertops, stainless steel appliances, under-cabinet lighting, a pantry with pull-out shelves, recessed lighting, and a breakfast bar with seating for four. Adjacent to the kitchen, the large utility/laundry room includes a washer and dryer and offers generous built-in cabinetry to meet all your storage needs. The spacious primary suite easily accommodates a king-size bed and offers privacy and comfort. Its luxurious ensuite bath, renovated in 2023, includes designer-grade white and gray tile, a frameless glass shower with dual shower heads, quartz countertops and backsplash, and a skylight that brings in soft natural light. Two additional bedrooms are thoughtfully separated from the primary suite and share an updated hall bath, remodeled in 2019 with a modern white vanity, quartz countertops, and contemporary finishes. Outdoors, enjoy a beautifully landscaped and spacious corner lot filled with mature greenery—including your own orange tree. The side-entry driveway leads to a two-car garage and features built-in cabinetry, an automatic garage door opener, and a Tesla charging station(installed in 2023), all adding to the home’s practical appeal. Located just 10 minutes from Park Avenue’s shops and restaurants and only 25 minutes from Orlando International Airport, this home is close to UCF, Full Sail University, Rollins College, AdventHealth facilities, and the Crosby Wellness Center/ Center for Health and Wellbeing. You'll also enjoy easy access to Winter Park Pines Golf Course and can walk to Cady Way Park, pool, trails, tennis courts, and pickleball courts. Zoned for top A-rated Winter Park schools—Aloma Elementary, Glenridge Middle, and Winter Park High—this home offers the ideal blend of convenience, community, and lifestyle in one of Central Florida’s most desirable areas. ROOF - 2013, HVAC - 2023, ELECTRICAL - 2023, WATER HEATER - 2025

101 S Ranger Boulevard, Winter Park
$401,000
Lakemont Heights SubDv. ⋅ 32792 Zip Code
Build your dream home in the heart of Winter Park! Located on the highly desirable Palmer Avenue, this premium lot offers a rare opportunity to create a custom residence just minutes from Park Avenue, Rollins College, top-rated schools, and the Winter Park Chain of Lakes. Situated among multi-million-dollar homes, this property is ideal for discerning buyers or builders seeking a great address and walkable lifestyle. Enjoy the charm of tree-lined streets, nearby boutiques, fine dining, and the cultural richness that makes Winter Park one of Central Florida’s most sought-after communities. Please note: The existing structure holds no contributory value and access to the interior is not permitted. This sale is strictly for the value of the land and location.

1809 Palmer Avenue, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Cedar Ridge Unit 1 SubDv. ⋅ 32792 Zip Code
Newly renovated 3 Bedroom 2 Bath in a well establish community of Cedar Ridge. Conveniently located in Winter Park Seminole County. Pool home. The office can easily turn into a 4th bedroom if needed. New tile floors throughout. Open, airy and bright. Updated kitchen with quartz countertop. New stainless steel appliances. New roof 2024, new water heater 2024, whole house plumbing re-piped 2025, electrical panels will be replace prior to closing, and most of the windows are newly replaced/repaired. Spacious Master Bedroom. Oversized 2 car garage attached. No Homeowners Association. Short drive to Park Avenue, Rollins College, UCF and 436.

1932 Houndslake Drive, Winter Park
$460,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code
Welcome to your Winter Park retreat! This spacious single-story ranch offers nearly 2,000 sq. ft. of living space with 3 bedrooms, 2 baths, and a versatile bonus room. The updated kitchen boasts granite counters, stainless steel appliances, and a cozy breakfast area, opening into a bright Florida room perfect for entertaining. The split floor plan ensures privacy, with a generous primary suite featuring a walk-in closet. HVAC about 3 years old and Roof was replaced in 2021 Outside, enjoy a fully fenced yard, ideal for pets and gatherings, plus a 2-car garage and low-maintenance concrete block construction. Zoned for top-rated Winter Park schools—Aloma Elementary, Glenridge Middle, and Winter Park High—this home offers both comfort and convenience. Just minutes from shopping, dining, and parks, this property blends location, lifestyle, and value in one of Central Florida’s most sought-after communities. Don’t miss this move-in ready gem!

2831 Lion Heart Road, Winter Park
$440,000
5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income. The main home features a freshly painted interior and exterior, new LVP flooring throughout, and a completely remodeled kitchen with new appliances. The primary suite includes an en suite bath that has been remodeled, and three additional bedrooms provide ample space for family or home office needs. Enjoy the Florida room overlooking a fenced, private backyard, perfect for entertaining. Roof replaced in 2024. A/C replaced in 2016. Zoned for top-rated Winter Park High School and conveniently located near Park Ave, shopping, dining, Costco, and major roadways. Move-in ready with room to personalize. Don't miss this versatile and rare Winter Park find!

3642 Periwinkle Drive, Winter Park
$290,000
3 Beds ⋅ 2 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code
Welcome home to 1920 Carrigan Avenue! Located in the highly desirable Winter Park section of Seminole County, this beautifully updated 3-bedroom, 2-bathroom home sits on an oversized 0.22-acre lot with mature trees and no HOA. Inside, you’ll find a modern and inviting space featuring remodeled bathrooms, an updated kitchen with stainless steel appliances, stylish laminate flooring, and fresh paint both inside and out. Major updates include a new AC system in 2023 and PEX piping throughout, offering peace of mind for years to come. Tucked away on a quiet dead-end street, this home is zoned for top-rated Seminole County schools and just minutes from Park Avenue, Winter Park Village, Rollins College, and major roadways like 436, I-4, and 417. Commuting to Downtown Orlando or Orlando International Airport is a breeze. With its unbeatable location, and no HOA fees, this is a rare opportunity you won’t want to miss.

1920 Carrigan Avenue, Winter Park