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3159 Greenwood Street, Winter Park
$285,000
2 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 2 SubDv. ⋅ 32792 Zip Code
Location truly matters—and this Winter Park gem delivers. This beautifully maintained 2-bedroom, 2-bath townhouse offers charm, functionality, and a rare bonus: a spacious screened-in lanai and private yard. Tucked within a well-established neighborhood, the home provides a peaceful residential setting while keeping you just minutes from everything Winter Park has to offer. Inside, you’ll find a stunning kitchen with stainless steel appliances, upgraded flooring, and modern countertops—making this home completely move-in ready. Whether you're searching for a primary residence or a smart investment, this property offers the perfect blend of comfort, flexibility, and convenience. Ideally located near Downtown Winter Park, Park Avenue, Rollins College, AdventHealth Winter Park, major highways, shopping, dining, and entertainment. You’ll also enjoy easy access to Downtown Orlando, Baldwin Park, Full Sail University, and Orlando International Airport. Opportunities like this are rare—schedule your private showing today.

3159 Greenwood Street, Winter Park
7796 Fernbrook Way, Winter Park
$285,000
3 Beds ⋅ 2 Baths ⋅ Fernbrook Trails Ph 3 SubDv. ⋅ 32792 Zip Code
Excellent price in Winter Park! On a quiet cul-de-sac in Seminole County just off Howell Branch Road, this inviting townhouse offers comfort and convenience in a desirable location. Inside, you’ll find a bright, spacious living room with large windows, a cozy dining nook adjacent to the kitchen with extensive cabinets, and a flexible first-floor third bedroom used as an office/gym that can easily convert to a bedroom again. Upstairs features generously sized bedrooms and a hall bath. The home has been recently painted inside and offers new laminate flooring upstairs, with tile and LVP throughout the main floor. Outside, enjoy a covered front porch, fenced backyard, storage shed and an extended driveway. The roof and air conditioner were replaced in 2018. With low monthly HOA dues of $110 that include lawn maintenance, this home offers easy, low-maintenance living. Along beautiful tree-lined streets with mature oak canopies, this neighborhood offers a peaceful, shaded setting that enhances everyday living. Conveniently just five miles from Park Avenue shopping and dining and three miles from Red Bug Lake Park, with quick access to SR 417, this home provides a balance of nearby amenities and quiet, established surroundings.

7796 Fernbrook Way, Winter Park
2653 Cayman Way, Winter Park
$284,000
3 Beds ⋅ 2 Baths ⋅ Windward Square SubDv. ⋅ 32792 Zip Code
All play and no work! This beautifully maintained 3-bedroom, 2-bath townhouse offers the perfect combination of comfort, convenience, low HOA fees, and an unbeatable Winter Park location. Whether you're a first-time homebuyer, downsizing, or looking for a low-maintenance lifestyle, this home checks all the boxes. Step inside to discover a bright, open floor plan highlighted by vaulted ceilings and dramatic clerestory windows that flood the home with natural light. The thoughtfully designed split-bedroom floor plan provides added privacy, while the spacious primary suite features a walk-in closet and sliding glass doors leading to your own private, fenced backyard. The kitchen offers a comfortable eat-in dining area, abundant cabinet space, and an oversized pantry for exceptional storage. An enclosed laundry room adds everyday convenience, while recent updates provide peace of mind, including a brand-new roof (2026), newer A/C, updated plumbing, updated electrical panels, and fresh interior paint. Step outside to your covered patio with a convenient storage closet, overlooking a fully fenced backyard—the perfect place to relax, entertain, or enjoy your morning coffee. With low HOA fees, you'll also enjoy outstanding community amenities, including three swimming pools, tennis courts, a playground, a clubhouse, and a private south gate providing quick and convenient access in and out of the community. Ideally located just minutes from Downtown Winter Park, you'll love being close to Park Avenue, shopping, dining, entertainment, top-rated schools, and major highways, making commuting throughout Central Florida quick and convenient. If you've been searching for an affordable, move-in-ready home with major system updates, fantastic amenities, low HOA fees, and an exceptional Winter Park location, this is the one you've been waiting for. Schedule your private showing today!

2653 Cayman Way, Winter Park
2006 Cornell Avenue, Winter Park
$280,000
2 Beds ⋅ 1 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code
Welcome home to this charming and fully remodeled 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. Located just minutes away from Downtown Orlando, Disney, Universal and Advent Health, this sought-after location offers convenience and comfort. This home boasts not only a prime location but also a cozy ambiance that will make you feel right at home. With its hardwood floors adding warmth and character, and the spacious fenced-in backyard providing privacy and room for outdoor activities, this property is ideal for those seeking the perks of Winter Park and College Park living as well as the fun outgoing, Orlando attractions.

2006 Cornell Avenue, Winter Park
5180 Lazy Oaks Drive Unit 5180, Winter Park
$280,000
2 Beds ⋅ 2 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Welcome to your Florida retreat. Whether you’re searching for the perfect first home or looking to downsize into a low-maintenance lifestyle, this single-story end-unit villa offers the ideal blend of comfort, convenience, and charm. With only one shared wall, it lives and feels like a single-family home. The HOA handles all exterior maintenance—including the roof, which was replaced just a few years ago—keeping your upkeep minimal and your insurance costs impressively low. The seller has lovingly maintained this home for nearly a decade and completed a long list of high-quality updates, including: - Glass sliders replaced in 2018 - Water heater replaced in 2019 - AC replaced in 2024 - Garage door replaced in 2024 - Front entry storm door added in 2024 - All kitchen appliances replaced within the last 5 years If that’s not pride of ownership, what is? Inside, the kitchen features newer cabinets, quartz countertops, and updated lighting throughout the home. The seller also transformed the back patio into a screened-in oasis—your own private Florida getaway perfect for morning coffee or evening relaxation. Location is another major highlight. Situated in prestigious Winter Park and zoned for some of Seminole County’s top-rated schools, this home offers unbeatable convenience. You’re just minutes from major highways, shopping, dining, and everything Central Florida has to offer. Schedule your showing today and experience all the beautiful features this home provides.

5180 Lazy Oaks Drive Unit 5180, Winter Park
5450 Peaco Place, Winter Park
$277,000
3 Beds ⋅ 2 Baths ⋅ Grand Pines SubDv. ⋅ 32792 Zip Code
Welcome Home! Winter Park property for under $300k! As you step up to this property you notice the fresh paint and the fresh mulch. Step into the home and you see consistent floor tile throughout the home as well as freshly painted walls. Take a step to the left and you see the large kitchen space to be able to freely move around as you cook. The primary bedroom is located in the rear and has access to the back yard. Bedroom sizes are a fair size. New garage door opener just installed This home is great for investors and also a GREAT WINTER PARK starter home. This property is close to highways, shopping and more! Welcome Home!

5450 Peaco Place, Winter Park
3321 Royal Street, Winter Park
$270,000
3 Beds ⋅ 2 Baths ⋅ Coronation Add SubDv. ⋅ 32792 Zip Code
Turnkey Charm in Winter Park! This beautifully remodeled 3-bedroom, 2-bathroom home offers the perfect blend of style and convenience. Step inside to find durable ceramic tile flooring flowing through a spacious family room, perfect for entertaining. The home features a 1-car garage with a functional laundry area equipped with a washer and dryer tucked neatly in the back, alongside a fantastic outdoor setup. Relax on your open, screened-in patio overlooking a massive, fully fenced backyard. Freshly updated inside and out, this move-in-ready gem is ready for its next owner!

3321 Royal Street, Winter Park
311 E Morse Boulevard Unit 6-12, Winter Park
$267,500
1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a surprisingly flexible layout. The current owner has creatively configured the space with separate living and dining areas, while the enclosed porch serves as a bedroom. The updated kitchen features decorative tile flooring, stainless steel appliances, and solid wood cabinetry. Sliding glass doors lead to a bonus room that can easily function as a home office, guest space, workout room, or additional living area. The bathroom includes a single vanity and tub/shower combination, and you'll appreciate the abundance of storage throughout the unit. One of the biggest advantages of this property is the peace of mind that comes with a monthly HOA fee that covers nearly everything—including electric, water, sewer, trash, building insurance, landscaping, pool maintenance, and on-site management. . Whispering Waters recently passed its structural integrity inspection and reserve study with excellent results, reflecting the care and quality of this well-managed community. Residents also enjoy access to beautiful Lake Osceola, where you can launch a kayak, relax by the water, or take in breathtaking sunset views. Whether you're looking for a full-time residence or a seasonal retreat this condo offers an unbeatable Winter Park location and true lock-and-leave convenience.

311 E Morse Boulevard Unit 6-12, Winter Park
5210 Lazy Oaks Drive, Winter Park
$266,500
2 Beds ⋅ 3 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. DISCOVER THE SERENE BEAUTY OF THIS WINTER PARK TWO-STORY TOWNHOME! Located in the SOUGHT-AFTER Lazy Oaks community. Blending contemporary style with everyday convenience, GORGEOUS 2-BEDROOM, 2.5-BATHROOM, 1-CAR GARAGE HOME. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. Cook like a pro in the BRAND NEW KITCHEN featuring NEW QUARTZ COUNTERTOPS and SLEEK STAINLESS STEEL APPLIANCES—perfect for culinary enthusiasts. This home is LOADED WITH UPGRADES, including: Newer Roof with 30-Year Shingles, New Laminate Flooring Throughout, Renovated Bathrooms with New vanities, Fresh Interior & Exterior Paint, New Light Fixtures, Faucets, Toilets, Water Heater from 2020, HVAC System from 2015. With affordable condo fees, this home offers both comfort and peace of mind. Located in a wonderful community, you'll enjoy easy access to shopping, major roads, and just minutes away from the vibrant Park Avenue. This move-in-ready home truly has it all! All measurements are approximate and should be verified by the buyer. Virtual Staging was added to some of the pictures.

5210 Lazy Oaks Drive, Winter Park
2302 Barbados Drive, Winter Park
$265,000
2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Welcome to Windward Square, a desirable Winter Park community conveniently located near shopping, dining, entertainment and major roadways. This spacious end-unit home offers 2 bedrooms, 2 full bathrooms with 1,544 square feet of living space. The home adds fabulous sun room with French doors to a private rear space. Originally designed as a 3-bedroom home, the third bedroom has been converted into a versatile flex room—ideal for a home office, den, hobby room or additional living space. The primary suite features a spacious walk-in closet with custom built-ins. Recent updates include a new roof in 2023, new flooring, fresh interior paint and more. As an end unit, the home provides additional privacy and a more open feel than interior units. The enclosed sunroom offers additional space for relaxing, entertaining or enjoying your morning coffee. Windward Square residents enjoy community amenities including a swimming pool and tennis courts. The convenient location provides easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this move-in-ready home offers space, flexibility and an excellent Winter Park location.

2302 Barbados Drive, Winter Park
2401 Sun Valley Circle Unit 2401, Winter Park
$265,000
2 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and unwind on the private back porch—an ideal outdoor sitting space. The kitchen features a pantry and cozy breakfast nook. The spacious primary suite includes a walk-in closet, updated bathroom, and direct access to the back patio. The second bedroom also offers new flooring and its own walk-in closet, making it perfect for guests or additional living space. With its inviting design and unbeatable location, this condo is a must-see—schedule your private showing today!

2401 Sun Valley Circle Unit 2401, Winter Park
2530 Leeward Way, Winter Park
$265,000
2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 1 SubDv. ⋅ 32792 Zip Code
Well-maintained 2-bedroom, 2-bath home with 1,199 sq ft in a desirable Winter Park 32792 location offering a fenced backyard, low HOA, and a flexible bonus space ideal for a home office, study, or hobby area. The functional split-bedroom layout provides privacy, while the open living and dining areas create a comfortable space for everyday living or entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly to the main living area plus upgraded appliances. The primary suite includes a private bath and generous closet space, while the secondary bedroom and full bath provide flexibility for guests, office use, or additional living needs. Enjoy outdoor living in the fully fenced yard—ideal for relaxing, gardening, or pets. Additional highlights include driveway parking, interior laundry, and low-maintenance living. -- NEW ROOF IN PROCESS -- Prime location with convenient access to major corridors and top destinations: ˜ 3 mi to Full Sail University, ˜ 5 mi to UCF, ˜ 4 mi to AdventHealth Winter Park, and ˜ 6 mi to Park Avenue and Downtown Winter Park. Nearby shopping, dining, and grocery options are within minutes, with quick connectivity to SR-436, University Blvd, and SR-417 for commuting throughout Central Florida. An excellent opportunity to own in Winter Park with space, privacy, and strong location value.

2530 Leeward Way, Winter Park
1500 Gay Road Unit 18D, Winter Park
$263,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
Welcome home to carefree lakefront living in the heart of Winter Park, where everyday life is complemented by breathtaking sunsets over beautiful Lake Killarney and one of Central Florida's most walkable locations. Nestled within the Chateaux Du Lac lakefront community, this beautifully updated second-floor condominium offers 2 bedrooms, 2 bathrooms, and an inviting open floor plan designed for comfortable everyday living. Stepping inside, plantation shutters throughout the home create a timeless look while allowing natural light to fill the space. The spacious living and dining areas flow seamlessly together, making entertaining both easy and enjoyable. The updated kitchen is sure to impress with quartz countertops, a center island, modern subway tile backsplash, stainless steel appliances, and recessed lighting that completes the contemporary design. The owner's suite provides a relaxing retreat complete with an updated ensuite bathroom featuring stunning floor-to-ceiling herringbone-style subway tile, an overhead rain showerhead, and modern finishes. The guest bedroom is generously sized and offers a large walk-in closet, while the second bathroom has been beautifully updated to match with the same designer tilework and rain showerhead. Sliding glass doors lead out to your private balcony, creating the perfect place to enjoy your morning coffee or unwind in the evening after a day on the lake. A brand-new water heater installed in 2026 provides added peace of mind. Residents of Chateaux Du Lac enjoy an exceptional lakefront lifestyle with access to a heated swimming pool, clubhouse, community deck overlooking Lake Killarney, private boat ramp, BBQ grilling area, saunas, kayak and paddleboard storage, and updated on-site laundry facilities. Whether you enjoy boating, skiing, paddleboarding, fishing, or simply taking in spectacular sunset views, this amenity-rich community offers everything you need to embrace the Florida lifestyle. Perfectly positioned just moments from Park Avenue, you'll enjoy easy access to locally owned restaurants, boutique shopping, cafés, Trader Joe's, the Winter Park Village, movie theater, farmers markets, and the nationally recognized Winter Park Sidewalk Art Festival. With convenient access to I-4, commuting throughout the Orlando area is effortless while still enjoying the charm and elegance that make Winter Park one of the area's most desirable communities. Schedule your showing today!

1500 Gay Road Unit 18D, Winter Park
642 Warrenton Road, Winter Park
$260,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Pines Patio Homes SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to 642 Warrenton Road! This freshly painted Winter Park home offers a spacious, light-filled interior with vaulted ceilings and an open layout designed for comfortable everyday living and is zoned for great schools. The generous living area features sliding glass doors that bring in abundant natural light through the dual panel sliding glass doors and provide direct access to the fully fenced backyard. The kitchen features warm wood cabinetry, light countertops, stainless steel appliances and a convenient breakfast bar overlooking the living space. Just beyond the kitchen, the dining area provides a dedicated space for everyday meals and entertaining. An interior laundry closet with washer and dryer adds extra convenience. Outdoor living is a highlight, with a private courtyard plus a fully fenced backyard surrounded by mature landscaping and plenty of green space for relaxing, gardening or entertaining. Enjoy low maintenance living as HOA includes lawn mowing. An attached garage provides additional parking and storage. Conveniently located in Winter Park with easy access to major roads including Semoran Boulevard, University Boulevard and Aloma Avenue, putting shopping, dining, schools and everyday conveniences within easy reach. With LOW HOA, this home combines generous living space, private outdoor areas and a convenient Central Florida location.

642 Warrenton Road, Winter Park
2384 Sun Valley Circle, Winter Park
$260,000
3 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Great opportunity to own this 3 bedrooms, 2 bathrooms single-story, ground level, end unit condo located within the quaint community of Cedarwood Village with a desirable Winter Park address! This light and bright home features vaulted ceilings in the living room, creating an open and airy feel. The kitchen offers an eat-in space, stainless steel appliances, a convenient pass through to the living room, and a laundry closet with washer and dryer included. Enjoy seamless indoor-outdoor living with sliding glass doors leading to a private rear screened-in lanai, plus an additional front patio just off the kitchen. Recent upgrades include new luxury vinyl flooring, a new roof (2023), new A/C ducts and insulation (2023), and full re-plumbing (2021), providing peace of mind for years to come. Two reserved parking spaces are located directly in front of the condo for added convenience. Community amenities include a pool, tennis court, and clubhouse. Ideally located near shopping and dining, Rollins College, Full Sail University, UCF, and major thoroughfares for easy commuting. This move-in ready condo offers comfort, convenience, and value in an unbeatable location!

2384 Sun Valley Circle, Winter Park
1952 Spring Street, Winter Park
$260,000
3 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 2 SubDv. ⋅ 32792 Zip Code
Discover the opportunity to own in Winter Park at 1952 Spring Street—a well loved 3-bedroom, 2-bath townhouse offering charm, functionality, and a private yard, a rare find in this desirable area. Nestled in a well-established neighborhood, this home provides a peaceful residential feel and tranquility while remaining just minutes from everything Winter Park has in store. The interior features new appliances, making it move-in ready with modern convenience. A brand-new roof will be installed once the property is under contract, offering added value and peace of mind to the future owner. Whether you’re seeking a primary residence or an investment opportunity, this property delivers flexibility, comfort, and location. Enjoy nearby parks, shopping, dining, and easy access to major roads—convenience meets lifestyle in one of Central Florida’s most sought-after communities. Don’t miss this exceptional opportunity—schedule your private showing today.

1952 Spring Street, Winter Park
1500 Gay Road Unit 24B, Winter Park
$255,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS! Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas! Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters, Stainless Steel Appliances, Raised Ceiling with Lighting, Kitchen Island/Bar! Enjoy the Ease of Luxury Vinyl Plank Flooring, Crown and Wide Floor Moldings, Plantation Shutters, Upgraded Energy Saving Windows and Sliding Glass Door. Modernized Master Bath with Raised Vanity, Open Layout with Spacious Shower with Seat and Barn Door for Privacy. Guest Bath also Updated with New Raised Vanity and Shower. Second Bedroom Walk-in Organized Closet. New Master Bedroom Carpet in 2025, New Water Heater in 8/2025 A/C replaced 4-5 years ago. Sit on Private Covered Patio and enjoy Pool Views and Landscaped Vistas. Walk to Shopping, Restaurants, Movies, Trader Joe's. Minutes from Park Avenue and Farmer's Market. Centrally located, close to I-4. One of Winter Park's "Best Kept Secrets"! Make an Appointment to view today!

1500 Gay Road Unit 24B, Winter Park
1960 Biscayne Drive, Winter Park
$250,000
2 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
Perfect Property for Builder or Investor Nestled in the sought-after Karolina on Killarney neighborhood, this classic 1935 bungalow offers timeless character and an exceptional opportunity to create your dream home in one of Central Florida's most desirable locations. Situated on a generous lot, this 2-bedroom, 1-bath residence features approximately 1,408 square feet of living space with a flexible floor plan ready for your personal vision. Original architectural details provide a warm foundation for renovation, restoration, or expansion, while the spacious backyard offers ample room for outdoor entertaining, gardening, or future additions. Whether you're a homeowner looking to customize a historic property or an investor seeking your next project, this home presents outstanding value in a neighborhood surrounded by beautifully updated residences. Ideally located just minutes from Park Avenue's renowned dining, boutique shopping, museums, and year-round events, you'll also enjoy convenient access to Downtown Orlando, College Park, Winter Park Village, major hospitals, and top commuter routes. With no HOA and a prime location in the heart of Winter Park, opportunities like this are increasingly rare. Bring your imagination and unlock the incredible potential this charming property has to offer!

1960 Biscayne Drive, Winter Park
2651 Cayman Way, Winter Park
$250,000
2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 2 SubDv. ⋅ 32792 Zip Code
Virtually Staged. ALL PLAY and NO WORK! Imagine coming home to a space where weekends are made for relaxing, entertaining, and enjoying the best of Florida living. This single-story, two-bedroom, two-bath townhome offers an effortless lifestyle in a location that puts everything within reach. Vaulted ceilings create an open, airy feel in the spacious living and dining area, while sliding glass doors lead to a private, fenced backyard with a large concrete patio?perfect for morning coffee, weekend barbecues, or unwinding after a long day. With no rear neighbors and views of the community green space, you?ll enjoy added privacy and tranquility. The kitchen is designed for everyday ease, featuring ample cabinetry, a breakfast bar, and all appliances included, making move-in simple. Retreat to the oversized primary suite with a walk-in closet and direct patio access, creating a true indoor-outdoor flow. The second bedroom offers flexibility for guests, a home office, or creative space. Step outside your front door and enjoy resort-style amenities, including three swimming pools, tennis courts, a clubhouse, and a playground—all with low HOA fees. With parking for three vehicles, convenience is built right in. Located close to shopping, dining, major roadways, and just minutes from Winter Park’s Park Avenue, this home delivers both comfort and connection. Owner-occupant only community—ideal for those looking to put down roots and enjoy a true neighborhood feel. Live more. Maintain less. Welcome home.

2651 Cayman Way, Winter Park
7487 Canford Court Unit 5, Winter Park
$247,500
4 Beds ⋅ 3 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code
OWNER FINANCE may be available with down payment. Unique 4 Bedroom 3 bath unit. Perfect for investors looking to rent to college attendees at UCF and surrounding or for larger families needing 4th bedroom. Lots of upgrades including 2 new bathrooms, new laundry room, new flooring and lots of new paint. Brand new AC system installed in 2025 and hot water heater in 2022. Granite counters, stainless appliances, ceiling fans and tons of storage. Rear screened and covered lanai off living room, covered and open rear private yard/ garden off kitchen and private balcony off master bedroom. Minutes to UCF, lots of shopping and all major highways

7487 Canford Court Unit 5, Winter Park
3484 Seagrape Drive, Winter Park
$246,200
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Charming 4-bedroom, 2-bath single-story home in the established Eastbrook neighborhood of Winter Park. Built in 1959 and situated on a 0.19-acre lot, this home features an open living and kitchen area with vaulted ceilings and wood-look laminate flooring. The kitchen offers stainless steel range and microwave, tile countertops, and tile backsplash. All bedrooms feature carpet and ceiling fans, with the primary suite offering an en-suite bath with a walk-in tiled shower. Enjoy the covered back patio and fully fenced backyard. Roof is approximately 5 years old. Interior laundry closet. Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High.

3484 Seagrape Drive, Winter Park
2168 Ridge Drive, Winter Park
$245,000
3 Beds ⋅ 1 Baths ⋅ Ridge High 1st Add SubDv. ⋅ 32792 Zip Code
Virtually Staged. Prime Winter Park Opportunity – Original Terrazzo Floors, Solid Block Construction & Endless Potential Discover an exceptional opportunity to own a classic Winter Park home priced at just $299,000. Situated on a generous 0.20-acre lot, this 3-bedroom, 1-bath concrete block home offers 1,208 square feet of living space and the perfect foundation to create your dream home or next investment. Built in 1960, this home showcases beautiful original terrazzo floors, a timeless feature that has become increasingly desirable and can be restored to complement today's popular mid-century modern and contemporary designs. The functional floor plan, abundant natural light, and solid construction provide the ideal canvas for renovation while preserving the home's authentic character. Major improvements have already been completed, including a roof replacement in 2021 and an HVAC system installed in 2018, allowing the next owner to focus on bringing their personal vision to life. To help buyers visualize the possibilities, one of the listing photos features an AI-generated renovation concept illustrating the home's exciting transformation potential. Location is everything, and this home delivers. Nestled in one of Central Florida's most sought-after communities, you'll enjoy convenient access to Downtown Winter Park, Park Avenue, Baldwin Park, Winter Park Village, Rollins College, AdventHealth, top-rated dining, shopping, parks, and major roadways. Whether you're looking to restore a classic mid-century home, renovate for resale, or customize a home that's uniquely your own, opportunities like this under $300k in Winter Park are becoming increasingly rare. Bring your vision and unlock the incredible potential of this Winter Park gem.

2168 Ridge Drive, Winter Park
5444 Peaco Place, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ Grand Pines SubDv. ⋅ 32792 Zip Code
WELCOME HOME!!! This CHARMING refreshed WINTER PARK GEM 2/2 is ready for YOU! Roof is 2024!!! FRESHLY PAINTED inside and out! As you drive up to the home you see the freshly mulched front of the home. Make you way into the front door and you see the open floor plan. The first thing you notice is the consistent floor throughout the living space in the home. the kitchen offers plenty of cabinet space to work with & NEW COUNTERTOPS! As you walk this home you notice it is in MOVE IN CONDITION and all you need to do is bring your furniture! The LARGE backyard is fenced in and offers options for pets and little ones to run free and play. There are 2 cement pads in the back ready to put patio furniture to sit and relax after a hard day at work. This home is conveniently located close to shopping, restaurants , the highway and more! WELCOME HOME!!!

5444 Peaco Place, Winter Park
700 Melrose Avenue Unit K25, Winter Park
$245,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Bright, beautifully updated 1-bed/1-bath condo with floor-to-ceiling views and a prime walkable location in the heart of Winter Park. The renovated kitchen and bath shine with modern finishes, while expansive windows frame serene, ever-changing views of the lushly landscaped grounds. Set within the sought-after Winter Park Gardens, residents enjoy 8 acres of private tropical gardens, peaceful walking paths, and a resort-style pool — all just steps from Park Avenue's dining, boutiques, and culture. A rare combination of tranquil garden living and unbeatable urban convenience. This is a 55+ community with room for younger owners. Call list agents for details.

700 Melrose Avenue Unit K25, Winter Park
1500 Gay Road Unit 20D, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
DRASTIC PRICE REDUCTION! LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA. CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE. BRIGHT SUN-FILLED 2 BEDROOM, 2 BATH USTAIRS UNIT WITH AN OPEN FLOOR PLAN AND PRIVATE BALCONY. THE PRIMARY BEDROOM IS A SUITE, AND THE SECOND BEDROOM FEATURES A SPACIOUS WALK-IN CLOSET. SOFT, WARM COLORS, TILE AND LUXURY VINYL FLOORS, RAISED KITCHEN CEILING AND GRANITE COUNTER ENHANCE THE SPACE. BRAND NEW WATER HEATER 6/2026! LARGE ROOMS MAKE IT EASY TO ARRANGE FURNITURE. ENJOY BOATING, SKIING AND WILDLIFE OF LAKE LIVING. COMMUNITY DECK, BOAT RAMP, HEATED POOL AND SAUNAS. MAKE AN APPOINTMENT TODAY TO SEE WINTER PARK'S BEST KEP SECRET!

1500 Gay Road Unit 20D, Winter Park
2433 Grand Teton Circle, Winter Park
$240,750
3 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to 2433 Grand Teton Circle in the sought-after Cedarwood Village community of Winter Park, where move-in ready living, thoughtful updates, and an unbeatable location come together. Featuring the largest floor plan in the community, this spacious condo has been refreshed with brand-new carpet and fresh interior paint, offering a bright, inviting space that’s ready for its next owner. The highly desirable layout includes a first-floor primary suite, making everyday living both comfortable and convenient. Inside, you’ll love the soaring vaulted ceilings that create an open, airy feel, while the wood-burning fireplace serves as the focal point of the living room, adding warmth and character. Just off the primary suite, a private front patio provides the perfect place to enjoy your morning coffee or unwind in the evening. A dedicated storage room offers additional space for seasonal décor, bicycles, and outdoor equipment. Cedarwood Village is known for its low-maintenance lifestyle, with the HOA maintaining the grounds and completing roof and exterior paint replacements approximately five years ago. Residents also enjoy access to a community pool, clubhouse, tennis courts, pickleball courts and guest parking. Location is one of this home’s greatest features. Ideally situated near Downtown Winter Park, Park Avenue, Winter Park Village, Baldwin Park, Full Sail University, Rollins College, Valencia College, and the University of Central Florida (UCF), you’ll enjoy convenient access to some of Central Florida’s best shopping, dining, entertainment, and recreation. Commuting is easy with nearby Howell Branch Road, Semoran Boulevard (SR 436), Aloma Avenue (SR 426), 417, and I4, providing quick access to Downtown Orlando, Maitland, Lake Mary, AdventHealth Winter Park, and Orlando International Airport. Located within the Seminole County Public School district, this home offers both convenience and an exceptional Winter Park address. Whether you’re searching for a primary residence, a low-maintenance home, or a spacious Winter Park condo in one of Central Florida’s most convenient locations, 2433 Grand Teton Circle offers the perfect combination of space, comfort, and lifestyle.

2433 Grand Teton Circle, Winter Park
1974 Staunton Avenue, Winter Park
$240,000
2 Beds ⋅ 1 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
SF home for sale.

1974 Staunton Avenue, Winter Park
2500 Lee Road Unit 229, Winter Park
$237,500
2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has been improved with raised Ceilings and expansive Wood Cabinets, Corian Sink and Countertops, Stainless Steel Appliances and expanded Pass-through Opening/Bar to Dining Room. Spacious Living and Dining Rooms with Lakeview. French Doors to Second Bedroom/Office with closets. Master Bedroom with en-suite Bath. Beautiful Cork Floors installed in all Living Areas. Tile in Kitchen and Baths. Ventless Washer and Dryer installed in Unit. Newer Double-Paned Energy-Efficient Windows. Unit has been replumbed. approximately 5 years ago. A/C and Water Heater new in 2025. Electric Panel replaced in 2019. You will love this close-in Winter Park Lakefront Community with all it's amenities, including Boat Ramp, 12 Boat Slips with Docks available for Lease to Owners, Waterfront Gazebo, Pool and. Clubhouse. Close to Shopping, Restaurants, Movie Theaters, Trader Joe's, Downtown Winter Park and Farmer's Market. Easy Access to I-4. Don't miss another Sunset! Call for a Private showing today!

2500 Lee Road Unit 229, Winter Park
1500 Gay Road Unit 17D, Winter Park
$230,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
PRICE REDUCED TOTAL OF $25,000! AMAZING VALUE!!! Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in 2023, Range 2019, Refrigerator in 2020, A/C in 2020, Double-Pane Windows and Sliding Door in 2016, Updated Electric Panel, Replaced Ductwork and added Attic Insulation. Master Bath has Double-Sink Vanity. Guest Bath has newer Vanity and Retiled Shower with replaced Shower Pan. Unit recently Replumbed. Plantation Shutters, recently Repainted and Carpeted. Short Walk to Shopping, Restaurants, Theaters, and minutes to Park Avenue with it's Village Style Shopping, Central Park with Bandstand, Spring and Fall Art Festivals, Farmer's Market and Downtown Train Station. Drive into the Community, catch a view of the Lake, watch a Sunset on the Deck and you will know "you're Home"!

1500 Gay Road Unit 17D, Winter Park
1250 S Denning Drive Unit 117, Winter Park
$230,000
2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code
Remodeled two-bedroom, one-and-one-half-bath residence in the Mead Garden Condominium community. Spanning 908 square feet, this first-floor home features a move-in-ready interior with an open-concept layout, luxury vinyl plank flooring throughout, and in-unit washer and dryer hookups, a rare offering within the building, located in the half bath. The kitchen includes raised-panel cabinetry in a warm wood tone, a mosaic tile backsplash and black appliances, including a refrigerator, range and dishwasher. A curved island with additional storage provides space for casual dining and entertaining. The kitchen opens to the dining area and living room, highlighted by a chandelier and access to a sunroom with sliding glass doors overlooking the community pool and landscaped grounds. The primary bedroom offers natural light from a pool-facing window, a walk-in closet, and an en-suite bath with a walk-in shower featuring white subway tile and a black-and-white mosaic tile floor. The second bedroom provides flexible space for guests or a home office. A half bath includes a pedestal sink, decorative mirror and gold-tone fixtures. Additional features include crown molding, updated plumbing fixtures, new windows and a leaded-glass front entry door. Near Azalea Park, Seven Oaks Park, Mead Botanical Garden and the Orange Avenue district with dining and retail. Close to Rollins College and Park Avenue.

1250 S Denning Drive Unit 117, Winter Park

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