Location: Winter Park , 32789
Do Not Show Listings
1981 BLUE RIDGE RD, WINTER PARK, FL 32789
$1,150,0005 Days on yellowkey MLS ID: O6402961
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2750 Built: 1963 Tax: $11,270 (2025)Community: Timberlane ShoresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,270
Elementary School: Audubon Park K8
High School: Winter Park High
Tax Year: 2025
Middle School: None
Remarks: Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and kitchen are arranged in a way that supports an open and functional feel, making the home especially appealing for hosting and daily routines alike. The family room adds valuable extra living space and creates a natural hub for movie nights, casual gatherings, or a second lounge area. The floorplan also shows a sun room extending off the family room, giving the home even more flexibility for relaxing, hobbies, or enjoying a bright bonus space with views of the backyard. The bedroom layout is thoughtfully separated from the main entertaining areas, offering privacy and comfort. The primary suite is positioned apart from the secondary bedrooms and includes its own bath and closet space, creating a peaceful retreat within the home. Three additional bedrooms provide flexibility for guests, a home office, or changing household needs. Outside, the open patio and private yard add to the home’s lifestyle appeal, creating space to enjoy outdoor dining, weekend get-togethers, gardening, or quiet mornings in the Florida sunshine. Together with the interior layout, these outdoor features help make the home feel both versatile and welcoming. Located in Winter Park, the property is set in a highly desirable area known for its established residential feel, attractive surroundings, and convenient access to shopping, dining, parks, and everyday amenities. The neighborhood adds to the home’s appeal by offering both comfort and accessibility in one of Central Florida’s most sought-after locations. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
147 S INTERLACHEN AVE #202, WINTER PARK, FL 32789
$2,272,00095 Days on yellowkey MLS ID: L4959060
REDUCED by $178,000 (7.3%) on 05/02/2026
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3272 Built: 1990 Tax: $18,439 (2024)Community: 147 Interlachen PlaceCondo
Taxes:$18,439
Elementary School: None
High School: None
Tax Year: 2024
Remarks: Welcome to 147 Interlachen Place, Enjoy Winter Park's most desirable location! One block from Historic Park Avenue/Central Park. Spacious, bright and all on ONE FLOOR. The buildings second floor offers privacy and easy access. The Southwest corner provides direct natural light throughout the day. Private elevator access with secured underground parking. This beautiful home offers a short walk to everything Winter Park, a pedestrian village of delight! Natural light fills the central courtyard which features an iron water fountain. Private pool with heated spa and outdoor grilling and entertaining area. Interior features include fireplaces in living room, 2 Southwest facing covered outdoor walkout balconies, accessed by living room, den, master bedroom and one directly over looking the pool. Master bathroom includes separate tub and shower, dual closets, split vanities and plenty of storage space. 4 full bath- 1 half bath (5). Two specified parking spaces also have large storage closets with security gate and elevator access to your floor. K-8 Audubon School district! Unit / building “horseshoe” configuration provides no neighbors on any of the 4 sides, courtyard interior, Private Luxury Living all on ONE floor!
Listing is courtesy of: HELLOSOLD LLC (954-778-5300)
Listing Agent: Dan Farber (954-778-5300)
1351 MAGNOLIA AVE, WINTER PARK, FL 32789
$3,100,0005 Days on yellowkey MLS ID: O6404105
0 Days Off yellowkey (back on 5/1/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3460 Built: 2026 Tax: $9,720 (2025)Community: Lake Knowles Terrace Add 02Single Family
Taxes:$9,720
Remarks: Under Construction. Just completed and ready to impress, this stunning custom-built residence delivers elevated design and effortless luxury in one of Winter Park’s most sought-after locations. Featuring 5 bedrooms and 4.5 bathrooms, this home blends timeless architecture with a fresh, curated aesthetic. From the moment you step inside, you’re greeted by warm wood flooring, custom millwork, and designer lighting that create a sophisticated, inviting atmosphere. The open-concept layout flows beautifully, centered around a showpiece kitchen with custom cabinetry, premium finishes, and an oversized island that anchors the space—perfect for gathering and entertaining. The great room is highlighted by a striking fireplace wall, adding depth and character. The first-floor primary suite offers a serene, private retreat, while a dedicated office with a full bath provides flexibility for guests or a refined work-from-home space. Upstairs, spacious secondary bedrooms and additional living areas offer comfort and privacy for family and visitors. Step outside to your own resort-style escape, complete with a sparkling pool, covered lanai, and fully equipped summer kitchen designed for seamless indoor-outdoor living. Ideally located just minutes from Park Avenue, top-rated schools, dining, and shopping, this newly completed home is a rare blend of style, comfort, and location.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
1695 LEE RD #B210, WINTER PARK, FL 32789
$109,000104 Days on yellowkey MLS ID: O6375872
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 638 Built: 1966 Tax: $1,493 (2024)Community: Waterfall CoveSpa: NoCondo
Taxes:$1,493
Remarks: This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and dryer. Assigned parkingspace. Community features swimming pool, tennis court and playground. Rent price includes use of the amenities, free basic cable TV, free internet, and pest control.
Listing is courtesy of: GM SUNSHINE REALTY LLC (407-376-1261)
Listing Agent: Giuseppina Moriconi (407-376-1261)
101 S NEW YORK AVE #302, WINTER PARK, FL 32789
$1,450,00042 Days on yellowkey MLS ID: O6390752
REDUCED by $130,000 (8.2%) on 04/24/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3174 Built: 2009Monthly Fee: $1,263 Tax: $19,802 (2025)Community: Winter Park ResidentialCondo
Taxes:$19,802
Remarks: Under contract-accepting backup offers. Motivated Sellers! Discover unparalleled luxury at The Douglas Grand, a distinguished location just a stone’s throw from Park Ave in Downtown Winter Park. This expansive 2-Story unit boasts 3,174 sq/ft of living space with your private elevator. From the moment you step inside, you’ll be captivated by the exquisite craftmanship and modern comforts that define this exceptional residence. This stunning condo boast three spacious ensuite bedrooms and abundance of storage. The heart of this home is the gourmet kitchen, custom-designed and built to fulfill every chef's dream complemented by top-of-the-line appliances that include a wall-mounted convection/microwave oven and a cutting-edge Wolfe induction stove top. The kitchen is not only functional but also perfect for entertaining, featuring a spacious breakfast bar where culinary creativity knows no bounds. As you move through this exceptional residence, in the living room, dining room, and entrance, creating an inviting ambiance that welcomes you home. Indulge in the spa-like sanctuary of the master bathroom, where luxury knows no bounds with a charming fireplace in the primary suite. Here, you'll find a sumptuous bathtub, separate vanity areas. With three generously appointed bedrooms, featuring custom closets, you'll have ample space to organize your wardrobe and storage needs effortlessly. Step onto the private balcony upstairs and be captivated by the breathtaking views. This secluded outdoor space is an ideal setting for unwinding with an evening cocktail, savoring a family dinner, or starting your day with a tranquil cup of morning coffee. The Douglas Grand enjoys a central location that places you within a lifestyle that defines this charming community. In addition to its unmatched location, this building offers a quiet, private, and secure environment—making it the perfect choice for those seeking a "lock and leave" second home or a luxurious vacation retreat. Don't miss this opportunity to experience the height of elegance and y reach of Downtown Winter Park's award-winning restaurants, cultural museums, upscale shopping boutiques, and the vibrant sophistication. Contact me today to schedule a private viewing of this remarkable residence.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Julie Scott (407-497-3492)
1836 GRINNELL TER, WINTER PARK, FL 32789
$1,050,00089 Days on yellowkey MLS ID: O6380457
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1907 Built: 1995 Tax: $11,979 (2025)Community: Lake VirginiaSingle Family
Taxes:$11,979
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring, recessed lighting, and all new modern fixtures. The entryway features comfortable seating, built in cabinets with an electric fireplace and wine refrigerator. The sleek, updated kitchen offers a gas range, stylish finishes and a functional layout perfect for everyday living and entertaining. Retreat to the spacious primary bedroom with a fabulous ensuite bath, complete with a soaking tub, dual vanities, a large separate shower, and a generous walk-in closet. A split-bedroom floor plan provides added privacy and comfort. The fully fenced backyard offers plenty of room for a pool and includes private parking for a boat on the side of the home. Whether you enjoy the home as it is or choose to build your dream residence, the possibilities are endless. New roof installed in 2022.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Cindy Kuykendall (407-718-3235)
150 DANA WAY, WINTER PARK, FL 32789
$3,799,00040 Days on yellowkey MLS ID: O6394012
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4451 Built: 2026 Tax: $14,010 (2025)Community: CharmontSpa: YesSingle Family
Taxes:$14,010
Middle School: Audubon Park K-8
Remarks: JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.
Listing Agent: Robert Kurzreiter Pa (407-476-4156)
2299 VIA TUSCANY, WINTER PARK, FL 32789
$2,200,000183 Days on yellowkey MLS ID: O6355858
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3986 Built: 1953 Tax: $13,185 (2025)Community: Maitland ShoresSingle Family
Taxes:$13,185
Elementary School: Dommerich Elem
Middle School: Maitland Middle
Remarks: Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes. Welcome to 2299 Via Tuscany, a gorgeous 4-bedroom, 3.5-bath home in the coveted Winter Park Vias. With 3,986 square feet on a 0.40-acre lot, it offers the perfect blend of luxury and comfort, featuring updated kitchens and baths, a new architectural shingle roof (2023), Pebble Tec-style pool finish, and lush landscaping. Inside, enjoy solid hardwood and modern tile floors, soaring ceilings, and two wood-burning fireplaces. The chef’s kitchen shines with SubZero refrigeration and a Viking 6-burner gas cooktop. The main floor offers a private primary suite, a guest suite, and a study/library with built-ins, while upstairs you’ll find two more bedrooms and a full bath. Modern perks include zoned A/C, a new EV charger, and epoxy-coated floors in the 2-car garage. Close to parks, the Racquet Club, and downtown Winter Park’s shops, dining, and culture, this home suits families and active lifestyles alike. Deeded lake access through the Maitland Shores Lakefront Preservation Association gives you a private ramp for kayaks, canoes, and more, plus easy access to schools, trails, and green spaces—a perfect mix of charm, amenities, and location.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Vincent Scarlatos (407-718-2378)
1781 INDIANA AVE #A, WINTER PARK, FL 32789
$545,00084 Days on yellowkey MLS ID: O6381195
REDUCED by $20,000 (3.5%) on 04/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1616 Built: 2008Monthly Fee: $464 Tax: $6,026 (2024)Community: Las Casas De IndianaTownhouse
Taxes:$6,026
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: 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.
Listing is courtesy of: CARLISLE REALTY, LLC (407-557-4024)
Listing Agent: James Rouadi (407-557-4024)
630 KILLARNEY BAY CT #3, WINTER PARK, FL 32789
$495,00097 Days on yellowkey MLS ID: O6375307
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1428 Built: 1986 Tax: $6,595 (2025)Community: Killarney Bay CondoCondo
Taxes:$6,595
Remarks: Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath, with a convenient half bath on the main level for guests. Enjoy community amenities including a swimming pool and a waterfront deck just 30 feet away, ideal for soaking in sunsets and lakeside breezes. All of this in an unbeatable location, just minutes from Winter Park Village, Trader Joe’s, dining, and shopping, with easy access to major roads for commuting.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)
Listing Agent: Anthony Consalvo (407-599-7070)
1354 INDIANA AVE, WINTER PARK, FL 32789
$589,90062 Days on yellowkey MLS ID: O6387500
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1269 Built: 1947 Tax: $5,352 (2024)Community: Metzingers AddSingle Family
Taxes:$5,352
Remarks: One or more photo(s) has been 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!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ellen Bessette (407-496-0076)
2779 SANBINA ST, WINTER PARK, FL 32789
$449,00054 Days on yellowkey MLS ID: O6388746
REDUCED by $11,000 (2.4%) on 04/29/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1405 Built: 1960 Tax: $5,629 (2024)Community: Howell HeightsSingle Family
Taxes:$5,629
Remarks: Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a formal dining room, which connects to a secondary living area perfect for entertaining. The open kitchen features granite countertops, stainless steel appliances, and a casual eat-in area, while refinished terrazzo floors run throughout the home adding character and easy-care durability that's quintessentially Florida. 2021 roof and HVAC mean the big-ticket items are already done. Step outside to a large screened-in patio overlooking a spacious backyard with plenty of room to add a pool or expand. One or more photo(s) was virtually staged. Minutes from Park Avenue and Downtown Winter Park's incredible restaurants and fantastic shopping, Rollins College, UCF, AdventHealth Winter Park, Downtown Orlando, and more. At $460,000 in 32789, this one won't last.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Caroline Fiore (407-538-2381)
525 OLOLU DR, WINTER PARK, FL 32789
$515,0006 Days on yellowkey MLS ID: S5148431
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1786 Built: 1966 Tax: $2,249 (2025)Community: Killarney CircleSingle Family
Taxes:$2,249
Remarks: Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern interior that is both visually appealing and highly practical for everyday living. The home features a completely updated kitchen with new cabinetry, brand new appliances, and a clean, contemporary design that integrates seamlessly with the main living areas. All bathrooms have been renovated, and new flooring has been installed throughout the home, creating a cohesive and polished environment. The layout has been optimized to provide comfort, flow, and usability, making the space feel open while still maintaining defined living areas. Additional improvements include updated front facing windows that enhance natural light, a new main entry door that strengthens curb appeal, and two A/C units offering efficient and flexible climate control. A detached storage structure adds valuable extra functionality, providing additional space for storage or utility use. Situated on a 0.21-acre lot, the property offers a balanced outdoor area with room for enjoyment, customization, or future enhancements. The lot configuration, which includes a portion of an adjacent lot, provides a sense of added space and flexibility not commonly found in similar properties within the area. Located in a well-established Winter Park neighborhood with consistent demand, the home benefits from convenient access to major roadways, shopping centers, dining, and key destinations. Its positioning makes it attractive for both owner occupants seeking a move-in ready home and investors looking for a well located asset with strong fundamentals. This is a property that delivers on both presentation and practicality an opportunity for buyers who recognize the value of thoughtful renovations, a strategic location, and a home that is ready to be enjoyed from day one while maintaining long term upside.
Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)
Listing Agent: Gisela Rojas (407-881-5278)
841 W SWOOPE AVE, WINTER PARK, FL 32789
$499,00097 Days on yellowkey MLS ID: O6373287
0 Days Off yellowkey (back on 4/30/2026)
REDUCED by $241,000 (32.6%) on 04/13/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1396 Built: 1930 Tax: $3,824 (2024)Community: Capens AddSingle Family
Taxes:$3,824
Remarks: This Winter Park property offers exceptional potential in one of the most desirable and rapidly evolving areas of Central Florida. Zoned R-3, this parcel opens the door to redevelopment possibilities for builders, investors, or end users looking to create something special. Ideally located just minutes from Park Avenue and within walking distance to Winter Park Village, you’ll enjoy easy access to premier dining, shopping, entertainment, and lifestyle amenities. The property is also conveniently situated near Orlando Avenue, providing quick connectivity to surrounding areas. The existing structure is being sold as-is, and the true value lies in the land, zoning, and prime location. With ongoing redevelopment nearby and strong demand for new construction, this is an ideal opportunity to build a custom residence or explore allowable uses under current zoning (buyer to verify all development potential with the City of Winter Park). Whether you’re a builder, investor, or buyer with vision, this is your chance to secure a property in a high-demand corridor with long-term upside.Cash buyers and builders welcome. No HOA. City water and sewer. 32789 zip code.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Evelyn Alicea (407-340-8154)
100 S INTERLACHEN AVE #101, WINTER PARK, FL 32789
$1,299,00076 Days on yellowkey MLS ID: O6382597
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1734 Built: 1971 Tax: $9,362 (2025)Community: Cloisters CondoCondo
Taxes:$9,362
Remarks: On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an award-winning luxury homebuilder, the residence features updated flooring, kitchen, baths, lighting and laundry. Wood flooring flows through the foyer, dining and living areas, while ceramic tile is installed in the bedrooms, and decorative tile in the baths. The kitchen is appointed with high-end appliances and custom solid wood cabinetry, designed for daily living and entertaining. The primary suite offers abundant natural light, a built-in closet and an en-suite bath with dual sinks, walk-in shower and a window providing natural illumination. A hall bath includes a tub-shower combination and additional storage. A sunroom off the third bedroom provides flexible space for a private office, den or reading room. The residence includes one assigned covered carport space and a dedicated climate-controlled storage unit on site. Two blocks from Park Avenue, residents enjoy convenient access to dining, shopping and cultural amenities in a lakefront community setting. The property presents an opportunity for full-time living, luxury downsizing or a lock-and-leave lifestyle in the heart of Winter Park.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Drew Henner (407-406-0662)
726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789
$1,185,9997 Days on yellowkey MLS ID: O6402984
Bed: 6 Bath: 0.0 Liv Area Sq Ft: 2282 Built: 2015 Tax: $5,170 (2025)Community: Morseland SubApartment
Taxes:$5,170
Elementary School: Lakemont Elem
Remarks: Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, and wood and tile flooring throughout, finishes that attract quality tenants while keeping maintenance straightforward. Private, fenced patios extend the living space outdoors, while in-unit laundry and ample parking add everyday convenience that renters actively prioritize. The location is the true driver, just steps from the Winter Park Golf Course and a short walk to Park Avenue’s dining, shopping, and lifestyle. This level of walkability continues to support strong tenant demand and long-term appreciation, particularly in the rapidly growing West End of Winter Park. As an added benefit, the property includes a membership to the Winter Park Country Club, further enhancing its appeal for both owners and tenants. For buyers looking to secure a property that offers immediate usability, consistent rental demand, and long-term upside in one of Central Florida’s most sought-after markets, this is a rare opportunity to check all three boxes in a single acquisition.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brandon Geers (941-928-5152)
1261 INDIANA AVE, WINTER PARK, FL 32789
$539,00016 Days on yellowkey MLS ID: O6400698
0 Days Off yellowkey (back on 4/29/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1660 Built: 2005Monthly Fee: $360 Tax: $2,892 (2025)Community: Townhomes/Harper PlaceTownhouse
Taxes:$2,892
Remarks: Under contract-accepting backup offers. Tucked in the heart of Harper Place, this 3-bedroom, 2.5 bath end unit townhome 1,660 sq ft of light-filled, low maintenance living in a thriving Winter Park location. The main level features a spacious living and dining room combo plus a separate family room and kitchen-perfect for entertaining. The kitchen includes a gas cooktop and range, granite counters, island, breakfast nook, and built-in cabinetry and desk. French doors open to a private side patio ideal for relaxing, pot gardening or grilling. The interior laundry off the kitchen leads out to the functional 2-car garage. Upstairs, the primary bedroom has a walk-in closet. The primary bath has a walk-in shower. Two secondary bedrooms offer flex space and share a bath with a tub shower. Wood floors downstairs and carpet upstairs. Recent updates include roof and gutters in 2022, exterior paint in 2023 and water heater in 2024. Community improvements continue with road resealing in the Spring of 2026, enhancing a well-kept neighborhood. 1261 Indiana is a great fit for a buyer seeking comfort, urban convenience, and a simplified lifestyle. Close to 1-4, shops, restaurants, hospital, and museums.
Listing Agent: Megan Cross (407-353-9997)
1529 HOLTS GROVE CIR, WINTER PARK, FL 32789
$2,795,00035 Days on yellowkey MLS ID: O6395062
REDUCED by $55,000 (1.9%) on 04/21/2026
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4356 Built: 2005Monthly Fee: $262 Tax: $21,342 (2025)Community: Windsong Lakeside Sec 02 43/71Spa: YesSingle Family
Taxes:$21,342
Remarks: Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Kristin Vogt Pllc (407-417-7206)
420 OHIO ST, WINTER PARK, FL 32789
$1,360,0008 Days on yellowkey MLS ID: O6399541
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3735 Built: 2026 Tax: $1,281 (2025)Community: Karolina On KillarneySingle Family
Taxes:$1,281
Remarks: Pre-Construction. To be built. On a prominent corner lot in the evolving Killarney neighborhood, this offering presents a rare chance to create a custom residence in the heart of the 32789 zip code. Set among a mix of established homes and new construction, the setting reflects the ongoing transformation of the area while remaining close to the amenities that define Winter Park living. The proposed plan features over 3,700 square feet of living space with a layout designed for both everyday comfort and entertaining. Current plans accommodate five bedrooms, five and a half baths, and a dedicated office, with flexibility to tailor the design or incorporate an accessory dwelling unit (ADU) depending on buyer preferences and final approvals. The building process is structured to allow selections to be made through a private showroom experience, offering an opportunity to personalize finishes and design elements throughout. Inside, the home is envisioned with clean architectural lines and a focus on natural light. The kitchen is designed as a central gathering space with quartz countertops, custom cabinetry, and an oversized. The primary suite is planned as a private retreat with a spacious bath, dual vanities, a glass-enclosed shower, and curated tile finishes. Flooring is specified as wide-plank luxury vinyl throughout the main areas, combining durability with a warm, cohesive aesthetic. The lot size and configuration provide the option to design an outdoor living environment, including space for a future pool, subject to final plans. The location offers convenient access to Park Avenue, the Winter Park Chain of Lakes, I-4, and nearby medical facilities, with dining options such as Hillstone within close proximity. Offered at a starting price of $1,360,000, this to-be-built opportunity combines location, flexibility, and a structured customization process for buyers seeking new construction in a well-located, established area. Buyers should verify all specifications, plans, pricing, and timelines with the builder.
Listing Agent: Leighton Hope (407-619-7897)
352 CAMBRIDGE BLVD, WINTER PARK, FL 32789
$650,000104 Days on yellowkey MLS ID: O6375545
2 Days Off yellowkey (back on 3/11/2026)
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 1917 Built: 1920 Tax: $9,806 (2024)Community: Glencoe SubSingle Family
Taxes:$9,806
Remarks: Under contract-accepting backup offers. This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a dedicated study. A large screened-in front porch adds to the home’s classic charm and provides the perfect space to relax and unwind. Tucked away in the rear of the property there is both flexibility and income potential: a stylish studio office and a spacious one-bedroom unit complete with its own living area and separate loft. This property is ideal for investors, multi-generational living, or owner-occupants seeking strong rental returns. Located closely to beautiful Lake Killarney and conveniently situated near highways, restaurants, and shopping, this property combines charm, location, and income potential in one exceptional offering.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Karen Jacobs (407-579-0062)
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