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$540,000
3 Beds ⋅ 2 Baths ⋅ Unrecorded Plat SubDv. ⋅ 32789 Zip Code
MULTIPLE OFFERS RECEIVED. SELLER WILL REVIEW OFFERS ON MONDAY, AUGUST 3RD. Welcome to Winter Park and the beautiful and desirable Lake Killarney Shores Neighborhood. Available for the first time in 25 years, this home is nestled on an oversized .35 acre lot with plenty of room to store a boat along with deeded lake access to Lake Killarney and NO HOA!! This Classic Florida Home is filled with natural light and features a spacious floorplan including 3 Bedrooms, 2 Full Bathrooms along with a bonus room perfect for a home office, home gym or play-room, a wood-burning fireplace, a spacious dining room overlooking the expansive screened and covered back porch area. The kitchen features solid wood cabinetry, stainless steel appliances and granite counter tops and provides additional space for storage or an eat-in kitchen arrangement. Updates include HVAC and Duct Work (2018) Newer Roof (2018), Updated Electrical (2018), Newer Plumbing (2018), New Water Main from Street to the house and Updated Master Bath (2018). The expansive fully fenced back yard includes two storage sheds and mature landscaping perfect for family gatherings and entertaining. This home is conveniently located near Winter Park Village, Downtown Winter Park and Park Avenue with access to an array of dining and shopping options. This home also has easy access to the I-4 corridor making it an easy commute to just about anywhere in Orlando/Central Florida Area. With a blend of tasteful updates, timeless character and charm this is the perfect place to call home! Call today to schedule a private viewing!

228 Rippling Lane, Winter Park
$510,000
3 Beds ⋅ 3 Baths ⋅ Villas Of Aragon Condo SubDv. ⋅ 32789 Zip Code
Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value to be sold AS-IS for the seller's convenience and TLC needed. ** One Year AHS Home Warranty included.** Nestled between Denning Dr and Orlando Ave, this home is an easy walk to the vibrant charm of Park Avenue, and close to the Winter Park Library, SunRail, and Rollins College. Publix and restaurants are just down the street! The first floor is tiled, with foyer entry, and comfortable family/dining/kitchen living area complete with fireplace. Sliding doors lead to a private patio. Upstairs, the large primary suite is a nice retreat with high ceilings, double walk in closets, double vanity and ample sized shower. Two more bedrooms and another bath complete the 2nd floor. High end washer and dryer are included in the attached garage, and a full wall workshop is in the garage too. Call to see it today!

1061 Aragon Avenue Unit 1061, Winter Park
$525,000
3 Beds ⋅ 4 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.

1134 Washington Avenue Unit 13C, Winter Park
$569,000
3 Beds ⋅ 3 Baths ⋅ Fairshores Place SubDv. ⋅ 32789 Zip Code
Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park
$600,000
2 Beds ⋅ 2 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Location, location, location. Wonderful home located in Winter Park besides Baldwin Park. Live in this home now - or purchase for the property and build your custom home! The yard is large. Large shed in the yard to store all of your yard essentials. You will love the area and the convenience to what makes this area special...steps from East End Market, lots of amazing restaurants, shopping, Leu Gardens, and so much more. Updates to the home include: Roof: 2020, HVAC 2019, Elecrical - new utility box, Plumbing: re-plumbed Kitchen and both bathrooms. Welcome Home.

2824 Woodside Avenue, Winter Park
$575,000
2 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.

1122 Washington Avenue Unit 7B, Winter Park
$599,000
3 Beds ⋅ 2 Baths ⋅ Glencoe Subdivision SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Nested on a spacious, tree lined lot just steps from Lake Killarney, 2361 Roxbury Road offers a rare opportunity to create your dream home in one of Winter Park’s most convenient locations. Ideally situated just off Fairbanks Avenue with quick access to I-4 , this 3 bedroom, 2 bath residence features 1723 square feet of living space, solid plaster walls and mid century character. Built in 1951, the home showcases an original pine paneled ceiling in the living room, adding warmth and architectural charm. Two large, new Anderson windows fill the room with natural light and highlight the pool view. New Anderson exterior doors improve the homes security and efficiency. The expansive Florida room provides flexible space for entertaining or future updates. Major improvements include a resurfaced Gunite pool in pebble finish (2024), exterior paint (2024), new paver driveway (2024), roof (2020) and HVAC system (2019). The garage has been enclosed and currently serves as storage and utility space. Outside you’ll find a fully fenced backyard with plenty of room to enjoy the Florida lifestyle. Located on a large lot with sidewalks and mature trees, this home presents an excellent opportunity for buyers looking to personalize a property in a desirable Winter Park location. The septic system was pumped in 2026, providing peace of mind. Bring vision and make this home your own!

2361 Roxbury Road, Winter Park
$579,900
3 Beds ⋅ 2 Baths ⋅ Albert Lee Ridge Add 02 SubDv. ⋅ 32789 Zip Code
Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell for under $600,000. Tucked away in a peaceful, private setting, yet just minutes from Winter Park’s famed Park Ave, Winter Park Village, College Park and Downtown Orlando with numerous shopping and dining options making this property the perfect blend of seclusion and convenience. Built in 1957, this classic Florida ranch features 3 bedrooms and 2 bathrooms within 1,837 SF of living space. Major updates include a new roof in 2024 and HVAC in 2019. Step inside off the covered front porch to find spacious living and dining areas highlighted by charming built-in features and abundant natural light. At the heart of the home, the kitchen offers easy access to a generous walk-in pantry/utility room/laundry area. The adjoining family room opens to a covered back porch overlooking the expansive backyard and tranquil canal. Situated on a .40-acre lot, the property extends beyond the canal, creating a natural wooded buffer that enhances privacy and provides a serene backdrop. Whether you envision a pool, outdoor kitchen, garden, or entertaining space, the backyard offers endless possibilities to create your dream outdoor oasis (subject to municipal review and approvals). Lake Bell is a 36-acre spring-fed ski lake with an average depth of 12 feet, ideal for boating, skiing, kayaking, paddle boarding and enjoying the Florida lifestyle. Fishing enthusiasts will also appreciate the lake’s reputation for largemouth bass and bluegill. Other notable exterior highlights include fenced in backyard, covered front entry, two rear porches and 1-car carport. The home is on septic that has been well maintained and serviced annually. The location also offers quick access to Interstate 4 and close proximity to area hospitals, parks and cultural centers. Don’t miss this exceptional opportunity to own waterfront property in Winter Park/3789 at an incredible value!

1003 Lake Bell Drive, Winter Park
$550,000
3 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Welcome to 650 Douglas Avenue, a beautifully updated 3-bedroom, 2-bath home ideally situated in one of Winter Park’s most desirable locations. This move-in-ready residence features luxury vinyl plank flooring throughout, quartz countertops, updated bathrooms with upgraded tile, modern lighting and plumbing fixtures, fresh interior paint, and a complete appliance package including washer and dryer. Beyond the home’s tasteful updates, the location truly sets it apart. Enjoy being just minutes from the vibrant shops, restaurants, and community events of Hannibal Square and renowned Park Avenue. Spend weekends exploring Winter Park’s award-winning dining, boutique shopping, farmers markets, museums, and picturesque parks, all just moments from your doorstep. This home offers the perfect combination of modern updates, walkable convenience, and the unmatched Winter Park lifestyle. Schedule your private showing today.

650 Douglas Avenue, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Manor SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the oversized 76x133 lot, inviting front porch, and clean curb appeal set the tone. Inside, original terrazzo floors, vaulted ceilings, and a bright open great room create warmth, charm, and livability. French doors open to a screened porch overlooking the spacious backyard. The split-bedroom floor plan features two renovated bathrooms, while the redesigned kitchen offers brand-new appliances, cabinetry, and quartz countertops. A spacious 19x12 family room with tile flooring connects to a large inside laundry room with abundant storage and flexible workspace options. Beyond the visible updates, this home stands apart because so many of the expensive and often-overlooked improvements have already been done, including roof, plumbing re-pipe, electrical updates and full-house rewire, hurricane-impact windows, impact front and rear doors, new mini-split HVAC systems, cast iron drain replacement, interior and exterior paint, and more. A rare opportunity to own a thoughtfully improved home in one of Winter Park’s most desirable locations — with no HOA. WELCOME HOME!

2974 Chantilly Avenue, Winter Park
$550,000
3 Beds ⋅ 4 Baths ⋅ Urban Green 12 SubDv. ⋅ 32789 Zip Code
Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after Urban Green Community. Built in 2022, this move-in ready residence showcases sleek, contemporary finishes throughout all three levels. Step up to a welcoming covered and pavered front porch, fenced-in front yard, and into a thoughtfully designed layout. The first floor offers a private bedroom with its own walk in closet and ensuite—perfect for guests or a home office. On the second floor, enjoy open-concept living with a bright and airy great room featuring high ceilings, recessed lighting, and seamless access to an oversized balcony through sliding glass doors. The modern kitchen is a showstopper, complete with quartz countertops, stainless steel appliances, a walk-in pantry, white shaker cabinets and a large center island with breakfast bar seating. Upstairs, you'll find two additional bedrooms, including the spacious primary suite with a walk-in closet, double vanity, glass-enclosed shower, and built-in shelving. The third bedroom also includes its own ensuite for added privacy and comfort. Additional highlights include an oversized rear-entry 2-car garage, laundry room, ample storage, and low-maintenance living. Enjoy unbeatable proximity to I-4, Downtown Orlando, Dubsdread Golf Course, Rollins College, Park Avenue, and Winter Park Village—offering endless dining, shopping, and entertainment options. This modern gem offers the best of both worlds: a turnkey home in a central, vibrant location. Don’t miss your chance to own in one of Orlando’s most desirable areas!

1250 Formosa Avenue, Winter Park
$510,000
3 Beds ⋅ 2 Baths ⋅ Town/Winter Park SubDv. ⋅ 32789 Zip Code
LOCATION. LOCATION. LOCATION. Heres the thing; in Winter Park, that's not a cliché. It's everything. There are homes in Central Florida that require a car for everything. This is not one of them. 641 West Lyman Avenue doesn't sit near Hannibal Square. It sits on it. This corner lot property is literally at the edge of one of Winter Park's most beloved and walkable districts — a place that draws residents and visitors alike with its brick-lined streets, acclaimed restaurants, wine bars, local boutiques, and genuine sense of community. Step outside your front door and within minutes you're at The Ravenous Pig, Prato, Chez Vincent, Park Avenue Tavern, Vinia Wine Bar, or CFS Coffee. The Saturday Farmers Market, the Hannibal Square Heritage Center, and the energy of one of Central Florida's most distinctive neighborhoods are all right here. And Park Avenue — Winter Park's crown jewel — is just a quick walk beyond that. Then there's Rollins College. Florida's oldest private university, founded in 1885, is an easy walk from your front door. Whether that matters to you as a parent, a professional, a culture enthusiast, or simply someone who values the intellectual and artistic energy a college campus brings to a neighborhood, this proximity is rare. You don't get Rollins-adjacent addresses very often — and when you do, they hold their value. And speaking of things that hold their value — the schools. This home is zoned for Winter Park High School, consistently rated one of the best public high schools in the state of Florida. Niche ranks it an A overall and among the top 5 public high schools in the entire Orlando metro area. It offers International Baccalaureate, Advanced Placement, and a college prep track that outperforms district and state averages across the board. For families, the school zone alone makes this address worth the conversation. The home itself is a clean, updated three-bedroom, two-bath bungalow — 1,120 square feet built in 2003, sitting on a corner lot enclosed by a white vinyl privacy fence. Inside, the sellers have done the work: new flooring throughout, new lighting, and all new appliances. There's nothing to fix, nothing to update, and nothing to negotiate around. You move in and you start living. That's the thing about this property. It's a turnkey home on the corner of one of Central Florida's most desirable walkable neighborhoods, in a school zone that parents actively relocate for, steps from a historic college campus and some of the best restaurants in the region. That combination, at this price point, inside the Winter Park city limits, simply does not come around often. Come see it before someone else does.

641 W Lyman Avenue, Winter Park
$599,999
Karolina On Killarney SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Rare opportunity to own a cleared waterfront lot on the shores of Lake Killarney in the heart of Winter Park. Spanning approximately .38 acres, this exceptional property offers stunning lake views and the potential for a future custom residence, subject to buyer verification of building requirements and intended use. Enjoy direct access to Lake Killarney while being just minutes from Park Avenue, Winter Park Village, top-rated dining, shopping, and major roadways.

1821 Killarney Drive, Winter Park
$625,000
3 Beds ⋅ 2 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code
Welcome to this BEAUTIFULLY MAINTAINED and thoughtfully upgraded 3-bedroom, 2-bath townhome in the exclusive Seville Park community of Winter Park, where timeless elegance, privacy, and exceptional craftsmanship come together in one truly special residence. Offering over 1,600 SQUARE FEET and originally built as the BUILDER'S OWN upgraded showcase unit, this home is nestled within an intimate enclave of just four townhomes and features the LARGEST ENCLOSED BACKYARD of the four. From the moment you arrive, the home makes a memorable impression with its GAS LANTERN LAMPPOST, charming walkway, and ELEGANT GLASS-PANEL FRONT DOOR. Step inside to discover soaring ceilings, crown molding, and rich wood flooring throughout, creating a warm yet elegant atmosphere filled with character and style. The Living Room is both inviting and dramatic, featuring a GAS FIREPLACE, oversized windows that flood the space with natural light, and French doors that open to the private outdoor patio and backyard retreat. The yard is enclosed by a IRON FENCE with GATED ENTRY, while MATURE BAMBOO lining the perimeter provides shade, privacy, and a tranquil ambiance rarely found in townhome living. The spacious Kitchen is a standout with 42-inch cabinetry, granite countertops, a HIGH-END THOR GAS RANGE, NEW WHIRLPOOL REFRIGERATOR, breakfast bar seating, and a closet pantry, combining luxury with functionality. The CHARMING DINING AREA adjacent to the Kitchen, is perfect for everyday dining and special occasions. A rare and highly desirable feature, the home offers a PRIMARY SUITE on the first floor, ideal for guests or multi-generational living, complete with its own en suite bath. Ascend the beautiful staircase accented with BRASS AND IRON RAILINGS to the impressive SECOND PRIMARY SUITE. This elegant retreat features a DRAMATIC BALCONY overlooking the Living Room below, a walk-in closet, and a spacious EN SUITE BATH with dual sinks, a garden tub, and a step-in shower. A third bedroom on the second floor offers its own unique charm with French doors opening to a PRIVATE ROOFTOP BALCONY—the perfect place to unwind and enjoy the peaceful surroundings. Additional upgrades include a NEW TILE ROOF (2022), touchscreen water heater, and RECENT REPIPING and REPLUMBING, offering both luxury and peace of mind. The 2-car garage includes BUILT-IN STORAGE CABINETS, and the driveway even features an extra dedicated parking space, an uncommon bonus in Winter Park. Located in one of Central Florida’s most sought-after areas, this home is zoned for TOP-RATED SCHOOLS and is JUST MINUTES from the boutiques, fine dining, and cultural attractions of Park Avenue and Hannibal Square. You’ll also enjoy CLOSE PROXIMITY to Rollins College, scenic parks, museums, farmers markets, and the renowned chain of lakes. With its designer upgrades, rare private outdoor space, elegant architectural details, and UNBEATABLE WINTER PARK LOCATION, this exceptional Seville Park townhome offers a lifestyle that is both refined and effortlessly inviting. Call and schedule your showing today!

962 Aragon Avenue, Winter Park
$540,000
3 Beds ⋅ 3 Baths ⋅ La Casas De Indiana SubDv. ⋅ 32789 Zip Code
Virtually Staged. Well-maintained townhome in Winter Park, ideally located near Park Avenue’s shops, restaurants, and everyday conveniences. The home features a bright, open floor plan with new luxury vinyl plank flooring throughout the main level. The kitchen has been updated with white cabinetry and newer appliances, offering a functional layout that flows seamlessly into the living and dining areas—well-suited for both daily living and entertaining. Upstairs, the bedrooms provide comfortable space with a practical and efficient layout. The primary bedroom includes an ensuite bathroom and a walk-in closet with built-in storage. The HOA covers roof, exterior maintenance, and landscaping, offering a low-maintenance ownership experience. Enjoy a fenced and enclosed back patio, creating a private outdoor setting ideal for entertaining, dining, or relaxing. In addition, the rear alley access offers a tucked-away, low-traffic environment with added flexibility and privacy. Additional features include a two-car garage and a central location with convenient access to major roadways, shopping, and dining.

1745 Indiana Avenue Unit J, Winter Park
$589,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

1319 Bessmor Road, Winter Park
$569,900
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

1741 Westchester Avenue, Winter Park
$560,000
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Sold data entry only.

1517 Harmon Avenue, Winter Park
$560,000
3 Beds ⋅ 2 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code
Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new windows (2019) a renovated primary bedroom and bath (2019), new septic drainfield (2023), tankless water heater (2019), new refrigerator (2024) and in ground pool converted to saltwater in 2023. A rare opportunity to own a classic Winter Park home in beautiful condition with modern improvements and exceptional outdoor living. Walk to Hunger Street Tacos, Lombardi’s Seafood and Creative Jane Art Studio while being conveniently located near 1-4, College Park and Winter Park. Come see this gem!

218 Orange Terrace Drive, Winter Park
$501,000
2 Beds ⋅ 2 Baths ⋅ Henkel Add SubDv. ⋅ 32789 Zip Code
Multiple Offers! Highest and Best due by 12:00pm on Tuesday 3/10! This impeccable townhome is located in sought after Winter Park. A lovely walkway brings you the front door, where you enter into the foyer of the home. The living room boasts loads of natural light from newer large picture windows, vaulted ceilings, newer porcelain floors and a French door which leads to the deck and backyard. The dining room is just beyond the living room where the peaceful views continue. The renovated kitchen features stainless-steel appliances, soft-close drawers and cabinets with pull-out shelving, Quartz counters and a quaint eat-in area. The staircase, with a large landing area, leads you into a generous size loft with a skylight that provides ample space for an office, workout space, or library. Just beyond the loft is the large primary suite complete with dual walk-in closets with closet systems and plenty of storage space, a private balcony overlooking the front of the home and an ensuite bathroom with a dual sink vanity, jetted garden tub and separate shower. A secondary bedroom space is located on the 1st floor along with a guest bathroom that offers a granite counter vanity and separate shower. The backyard is very Zen and includes 2 decks along with green space. Other amenities and updates include: newer roof, newer water heater, newer windows and sliding door and new porcelain floors. Welcome home!

1289 Harmon Avenue, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ Carver Town SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character while offering the lifestyle people move here for. This 3-bedroom, 2-bathroom home contains 1,356 square feet of thoughtfully updated living space designed for both comfort and style. From the moment you step inside, you'll notice the clean, modern feel created by zero carpet throughout the entire home, giving every room a fresh, cohesive look while making maintenance simple and practical. At the center of the home is the fully updated kitchen, featuring beautiful granite countertops, ample cabinetry, and a functional layout perfect for everyday living or entertaining guests. The kitchen serves as the heart of the home, separating the spacious living room from the formal dining room, creating a natural flow between gathering spaces while maintaining distinct areas for relaxing and hosting. Both bathrooms have been fully renovated, showcasing modern finishes that complement the home's updated aesthetic. Each bedroom offers comfortable space, natural light, and flexibility for a primary suite, guest room, or home office. Convenience continues with the laundry closet featuring a newer stackable washer and dryer, maximizing space while keeping everyday tasks simple and efficient. Step outside and you'll find a fully fenced backyard, providing privacy and plenty of room for pets, outdoor gatherings, or simply enjoying Florida’s beautiful weather. The property also includes an oversized covered carport, offering generous parking and protection from the elements. For electric vehicle owners, the carport is already equipped with a Tesla charger, making daily charging effortless and future-ready. What truly sets this property apart is its unbeatable location. Situated in historic Carver Town, you're just minutes from the charm and vibrancy of downtown Winter Park. Enjoy easy access to Park Avenue’s award-winning restaurants, boutique shopping, art galleries, and cultural attractions. Spend weekends exploring the Winter Park Farmers Market, taking a scenic boat tour on the Winter Park Chain of Lakes, or strolling through Central Park’s shaded oak-lined paths. Whether you're looking for a primary residence, a stylish Winter Park retreat, or a home close to everything that makes this city special, 720 W Webster Avenue delivers the perfect combination of location, updates, and lifestyle. Opportunities to own a fully renovated home this close to downtown Winter Park are rare. Schedule your private showing today and experience everything this exceptional property and location can provide!

720 W Webster Avenue, Winter Park
$574,900
3 Beds ⋅ 2 Baths ⋅ Metzingers Add SubDv. ⋅ 32789 Zip Code
Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!

1354 Indiana Avenue, Winter Park
$475,000
2 Beds ⋅ 1 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just one mile from Park Avenue, SunRail, and Rollins College, and only half a mile from Hannibal Square, local parks, and the Winter Park Library, this property offers an unbeatable blend of convenience, walkability, and lifestyle. As you step inside, you are greeted by a modern open floor plan enhanced with luxury vinyl plank flooring that flows seamlessly throughout the home. The spacious living and dining areas create an inviting environment ideal for both everyday living and entertaining. The updated kitchen serves as the heart of the home, featuring stainless steel appliances, granite countertops, and timeless white shaker cabinetry. Its thoughtful layout allows for easy conversation and connection while preparing meals, making it as functional as it is stylish. The oversized great room provides flexibility for relaxing, hosting guests, or creating a dedicated workspace. Both bedrooms are generously sized, offering comfort and versatility. The owner’s bedroom is especially appealing, complete with a custom closet organizer and direct access to a private paver patio—an ideal setting to enjoy Florida’s year-round sunshine. The bathroom has been tastefully updated with granite countertops and a shower/tub combination accented by classic white subway tile, creating a clean and timeless aesthetic. Outdoors, the secluded backyard offers privacy and future potential, with room to expand or customize according to your vision. Whether you are searching for a primary residence, a downsizing opportunity, or an investment in the heart of Winter Park, this property presents a rare chance to own a beautifully updated home in a prime location. Experience the charm, convenience, and lifestyle that 1036 Aragon Avenue has to offer. Schedule your private showing today.

1036 Aragon Avenue, Winter Park
$516,000
3 Beds ⋅ 3 Baths ⋅ Las Casas De Indiana SubDv. ⋅ 32789 Zip Code
Welcome to 1781 Indiana Avenue, Unit A, a beautifully appointed three-bedroom, two and a half bathroom townhouse nestled in the heart of Winter Park. This inviting residence offers the perfect blend of comfort and convenience, featuring a spacious two-car garage and a private courtyard ideal for morning coffee, outdoor dining, or relaxing in the Florida sunshine. Inside, the thoughtfully designed floor plan provides generous living spaces, well-proportioned bedrooms, and an effortless flow for everyday living and entertaining. Located just minutes from Winter Park’s renowned shopping, dining, parks, and top-rated schools, this home presents an exceptional opportunity to enjoy low-maintenance living in one of Central Florida’s most desirable neighborhoods.

1781 Indiana Avenue Unit A, Winter Park
$599,900
3 Beds ⋅ 2 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.

1951 Staunton Avenue, Winter Park
$585,000
2 Beds ⋅ 2 Baths ⋅ Andalucia Apts SubDv. ⋅ 32789 Zip Code
This move-in-ready condominium checks nearly every box for today’s buyer, offering a lock-and-leave lifestyle in an exceptional Winter Park location. The completely renovated two-bedroom, two-bath residence features high-quality finishes and thoughtful details throughout, including wide-plank white oak flooring and a bright, open-concept living space designed for everyday comfort and entertaining. The chef’s kitchen is stylish and functional, showcasing honed quartzite countertops, custom cabinetry extending to the ceiling, GE Café appliances with hood vent, and a handcrafted Moroccan Zellige tile backsplash. Both the primary suite and guest suite include custom built-in closets and private en-suite baths. Each bath has been fully updated with new vanities, designer tile, glass-enclosed showers and curated fixtures. A screened patio provides an inviting outdoor retreat, overlooking mature oak trees and lush landscaping. The first-floor location allows for easy access to assigned covered parking and an exterior storage unit just near the front door. Recent updates include a new roof (2024), new HVAC system (2023), new water heater (2023), rewired electrical and refreshed exterior paint (2018). An extraordinary setting places this residence just a short distance from Park Avenue and Central Park, the heart of downtown Winter Park. Enjoy a walkable lifestyle where mornings can begin with coffee at a local café, evenings are filled with dining, live music and community gatherings, and weekends are spent strolling the beloved Saturday Farmers’ Market. Central Park is home to cherished traditions including the Winter Park Sidewalk Art Festival, outdoor concerts, movies on the lawn and various holiday parades along Park Avenue, bringing energy and charm to the area throughout the year. Adding to the appeal, the home is also moments from the historic Winter Park 9 Golf Course, established in 1914 and recognized as one of the oldest municipal golf courses in Florida. Whether enjoying a round of golf, an evening walk, or simply taking in the surroundings, this location offers a rare blend of leisure, culture and convenience in one of Central Florida’s sought-after downtown environments.

535 N Interlachen Avenue Unit 106, Winter Park
$540,000
3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Beautifully situated on an elevated 50-by-106-foot lot in the Waterbridge community, this spacious single-story home enjoys a quiet cul-de-sac setting overlooking a small neighborhood park and is adjacent to a green space that enhances privacy. The property has wonderful curb appeal with mature trees, a wide driveway, an oversized two-car garage, and an inviting entrance courtyard that creates a sheltered transition into the home. Inside, the floor plan offers generous room sizes and excellent flow, beginning with a large foyer that opens to both the formal living room and the formal dining room. The 17’ x 12’ living room features a vaulted ceiling and large-format windows. The formal dining room is spacious and opens through sliding glass doors to a private side courtyard ideal for container gardening or quiet outdoor seating. The kitchen is sizable and well designed, with extensive counter space and abundant cabinetry, and offers convenient access to the side courtyard. The kitchen opens to the family room, allowing easy interaction between the two spaces, and extends into the Florida room beyond. The Florida room is one of the most charming areas of the home, with a brick façade along one wall, sliding glass doors, and views of the brick-covered and maturely landscaped backyard. This light-filled space is perfect for casual dining, a reading nook, or year-round indoor–outdoor living. The bedroom wing is thoughtfully spaced away from the main living areas. The primary suite is generously proportioned at roughly 21’ x 17’, with a vaulted ceiling, walk-in closet, and a spacious bathroom that includes a standalone tub, separate shower, long vanity with significant counter space, and a dedicated makeup area. Two additional bedrooms are comfortable in size with reach-in closets and share a full hallway bath with a long vanity and a tub-shower combination. Closet space and storage are abundant throughout the home, including hall storage, bedroom closets, built-ins, and a deep garage with workshop potential. Outdoor living is a highlight of the property. In addition to the front entrance courtyard and the private dining courtyard, the home features a lovely brick-paved backyard framed by mature landscaping, planting beds, and established greenery. The space is low-maintenance and provides multiple areas for seating, gardening, and relaxation. Recent updates include replacement of the electrical panels, which is set for final permit closing inspection; a 2017 HVAC; and a 2018 full home replumb. A current four-point inspection is available and will be updated to reflect the electrical panel replacement once the permit is closed. With its cul-de-sac location, elevated lot, multiple courtyards, flexible living areas, and desirable proximity to Park Avenue, Baldwin Park, the Cady Way Trail, the nearby dog park, and Downtown Orlando, the home enjoys an exceptional setting within a highly regarded Winter Park school zone. Meticulously maintained and built on excellent bones, it offers the uncommon opportunity to move right in or renovate with vision and create something extraordinary.

1817 Jessica Court, Winter Park
$622,500
2 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Welcome to 1835 Jessica Court in Winter Park’s highly desired Waterbridge community. This beautifully maintained 2-bedroom, 2-bath residence offers a spacious, well-designed interior and a private pool, creating an exceptional blend of comfort, quality, and effortless Florida living. Recent enhancements include Roof 2023, A/C 2024, Pool Pump 2023, Pool Filter 2024, new flooring, fresh interior paint, upgraded baseboards, and an updated vanity in the guest bathroom, giving the home a refined and refreshed feel throughout. The open layout provides flexible living and dining spaces suited for a variety of lifestyles, while the 2-car garage adds convenience and valuable storage. A screened back patio extends the living area and offers a comfortable outdoor space overlooking the private pool, designed for serene enjoyment with minimal upkeep. Waterbridge residents enjoy access to community tennis courts and walkable surroundings. Centrally located between Park Avenue, Baldwin Park, and Audubon Park, this home provides quick access to dining, boutique shopping, local markets, and outdoor recreation. Nearby schools include Brookshire Elementary, Glenridge Middle School, and Winter Park High. This property delivers a rare combination of updates, location, and ease in one of Winter Park’s most convenient and sought-after neighborhoods.

1835 Jessica Court, Winter Park
$567,500
3 Beds ⋅ 2 Baths ⋅ Seville Park SubDv. ⋅ 32789 Zip Code
Welcome to this charming 3 bedroom, 2 bathroom home in desirable Winter Park, Florida. With over 1450 square feet of living space, this property is perfect for families or individuals looking for a cozy yet spacious place to call home.Upon entering, you'll be greeted by bright and airy living spaces that flow seamlessly between the dining area, kitchen, and sunken living room. The updated kitchen features stainless steel appliances, granite counter tops, and pendant accent lighting over the bar. In this SPLIT floor plan, the master bedroom boasts an en-suite bathroom with ample closet space, while the two bedrooms are perfect for guests and/or a home office. The home is just steps away from Park Ave, Hannibal Square, Seven Oaks Park, and Mead Gardens. With so many dining and entertainment options right outside your front door, you'll be able to take advantage of everything Winter Park has to offer. All of these amazing features and amenities are also linked to Winter Park's highly sought after public schools.

1010 Aragon Avenue, Winter Park
$520,000
3 Beds ⋅ 2 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code
Mid-Century Modern Charm in the City of Winter Park! Enjoy living in one of the most sought after neighborhoods in Winter Park, adjacent to Baldwin Park and Audubon Park. This home blends timeless design with today’s updates—just minutes from shopping, dining, parks, and top-rated schools. Make this stylish retreat your own and experience the best of Winter Park living! Enjoy the comfort of this updated Mid-Century Modern home ready for you to make it your own! Featuring an oversized updated kitchen with a sleek black and stainless designed cabinet combination with frosted glass upper cabinets, and lots of granite countertops—perfect for entertaining or everyday living. All inclusive stainless steel appliances with a five-burner gas stove and hood and a breakfast bar with seating that flows into the bright and open great room. There the floor-to-ceiling windows make the room so special. The huge primary suite has double closets for lots of storage, room for a sitting area to relax and read or watch a show. The updated ensuite bath has a walk-in shower with beveled glass door and built-in shower seat. Other sought after features include an oversized walk-in pantry, large combined laundry/storage room, and covered carport. Newer double paned windows and sliders allow the home to be flooded with natural light, while a tankless water heater and recent AC adds modern efficiency.

3025 Northwood Boulevard, Winter Park