Location: Winter Park
Do Not Show Listings
2142 BLOSSOM LN, WINTER PARK, FL 32789
$399,90011 Days on yellowkey MLS ID: O6409144
0 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1363 Built: 1957 Tax: $2,217 (2025)Community: AcreageSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,217
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year: 2025
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. Exceptional opportunity to build new in one of Winter Park’s most desirable and established areas on the north shore of Lake Killarney. Situated on a spacious 0.34-acre lot, this property offers over one-third of an acre—providing ample room to design and construct a substantial custom home in a neighborhood known for its longtime charm, mature surroundings, and unbeatable location. With some homes nearby enjoying water access and lakefront settings, the area continues to be highly sought after for both renovation and new construction opportunities. Originally built in 1957, the existing ranch home is being offered for land value, presenting an ideal opportunity for builders, investors, or buyers looking to create their dream home in a prime Winter Park location. Perfectly positioned near Lee Road and I-4, the property offers quick access to downtown Winter Park, Park Avenue, Maitland, Orlando, top dining, shopping, entertainment, and everyday conveniences. Opportunities for oversized homesites in this location are becoming increasingly rare, especially in such a well-established and centrally located community. Whether you are a builder searching for your next project or a buyer looking to secure premium land in Winter Park, this property represents exceptional potential in a highly sought-after location.
Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)
Listing Agent: William Wygle (407-375-9005)
1946 STRATHAVEN RD, WINTER PARK, FL 32792
$675,0005 Days on yellowkey MLS ID: O6411329
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2102 Built: 1960 Tax: $8,540 (2025)Community: Kenilworth Shores Sec 07Single Family
Taxes:$8,540
Elementary School: Brookshire Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: ? FULLY REMODELED WINTER PARK POOL HOME NEAR BALDWIN PARK! ? Welcome to 1946 Strathaven Road — a beautifully updated 4-bedroom, 3-bath home with a dedicated office, ideally located near both Winter Park and the highly sought-after Baldwin Park community, known for its lakeside dining, walkability, parks, boutiques, and vibrant neighborhood atmosphere. ? This move-in ready home features an open and light-filled layout with designer finishes throughout, including updated flooring, custom cabinetry, modern lighting, and beautifully remodeled bathrooms and kitchen with premium appliances and upscale countertops. Major upgrades include a NEW roof (2023), windows (2023), water heater (2023), electrical panel (2023), plus updated plumbing and electrical throughout for true peace of mind. Enjoy spacious living areas, a luxurious primary suite, and a private backyard perfect for relaxing or entertaining. Conveniently located near top-rated schools, parks, shopping, dining, Park Avenue, and everything Winter Park living has to offer, this home combines modern updates with an unbeatable Central Florida location.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Youbel Montesino (954-608-4838)
316 BECKETT CT, WINTER PARK, FL 32792
$450,0005 Days on yellowkey MLS ID: O6411108
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1966 Tax: $2,232 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$2,232
Elementary School: None
High School: None
Middle School: None
Remarks: Opportunity knocks in one of Central Florida’s most sought-after locations! This 4-bedroom, 2-bath home at 316 Beckett Court has been completely demoed and is ready for your vision to come to life. Whether you’re an investor, builder, or buyer looking to create your dream home, this property offers the ultimate clean slate for a full renovation or custom redesign. Situated in highly desirable Winter Park, this property places you in the heart of one of Orlando’s premier communities, known for its tree-lined streets, charm, upscale shopping, dining, and cultural attractions. Enjoy easy access to Downtown Winter Park Historic District and iconic Park Avenue, home to boutique shopping, cafés, restaurants, and vibrant community events, along with the beauty of Central Park and the cultural appeal of The Charles Hosmer Morse Museum of American Art. Winter Park is also home to the prestigious Rollins College, adding to the area’s timeless character and desirability. Bring your contractor, your imagination, and your vision—properties with this kind of potential in Winter Park are rare. Endless possibilities await!
Listing is courtesy of: ITS REALTY (321-437-7363)
Listing Agent: Patrick Westervelt, Llc (407-533-1000)
1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789
$1,650,0005 Days on yellowkey MLS ID: O6407841
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2467 Built: 1964 Tax: $4,844 (2025)Community: South Lakemont ShoresSpa: NoSingle Family
Taxes:$4,844
Elementary School: Baldwin Park Elementary
Remarks: A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area and a wall of windows and doors leading to the lake. The island kitchen is a cook's dream with abundant workspace and welcoming island seating. Imagine waking up every morning to yet another amazing view- The primary suite is spacious and private with newer bath and large walk- in closet. Nicely appointed secondary bedrooms and updated baths. In addition to the main living area, there is a separate oversized family room with a full bath adjacent. This home is a perfect blend of classic architecture and carefully designed updates. Other features include two car garage with "glass" overhead doors and mini-split HVAC, metal roof, generous closets & storage throughout and recently installed sod. What makes this house truly special is the setting on Lake Spier- a ski lake tucked away in a secluded part of Old Winter Park . There are no homes across the lake- so spending time on the patio and dock offers an expansive view of water and trees and a remarkable sense of privacy. Inside and out, every space feels connected to the natural beauty. Great location to enjoy Winter Park living. Ideally situated near top rated schools - Baldwin Park, Glenridge and Winter Park High School. Enjoy close proximity to walking trails, restaurants and shopping. This home is truly special!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Nicole Seybold (407-808-9374)
1177 KENWOOD AVE, WINTER PARK, FL 32789
$1,800,00080 Days on yellowkey MLS ID: O6390592
0 Days Off yellowkey (back on 5/21/2026)
REDUCED by $70,000 (3.7%) on 05/13/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4363 Built: 2007 Tax: $16,206 (2025)Community: Dixie TerraceSpa: NoSingle Family
Taxes:$16,206
Remarks: Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat, complete with a walk-in closet and an en-suite bathroom featuring dual sinks, and a separate soaking Jacuzzi. Step outside to enjoy the covered patio—perfect for entertaining or unwinding. The backyard a outdoor escape with a sparkling in-ground pool and a fenced area for added versatility. Inside, the home has been refreshed with new interior paint and partial flooring updates, giving it a clean, updated feel. Don’t miss the opportunity to make this beautiful property your next home. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
450 LAKEWOOD DR, WINTER PARK, FL 32789
$2,500,00031 Days on yellowkey MLS ID: O6403490
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4572 Built: 2000 Tax: $11,393 (2025)Community: Osceola Shores Sec 03Single Family
Taxes:$11,393
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Vonda Fields (321-438-6906)
7794 COUNTRY PL #2, WINTER PARK, FL 32792
$237,00045 Days on yellowkey MLS ID: O6397587
REDUCED by $1,500 (0.6%) on 05/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1988Monthly Fee: $296 Tax: $2,620 (2024)Community: Goldenrod Villas CondoSpa: NoCondo
Taxes:$2,620
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: Winter Park Clean, UPDATED and in Move In Condition - The newest condo's year built are located on the last street in the complex where this unit is located which features a more contemporary open floor plan. Enjoy the One story living with no steps. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - PRIVATE!** Located second to the end of a Quiet Dead End Street. Step into a bright and airy condo featuring laminate and tile floors. Newer painted pastel colors throughout. The updated contemporary kitchen has NEWER Pecan colored cabinets and NEWER granite counter tops with stylish designer tile back splash. Both bathrooms have NEWER vanities and granite counter tops. The second bath features a granite top designer Pedestal vanity. The split bedroom floor plan that provides privacy, both bedrooms have spacious Walk-In closets. *** Open living area shines with natural sun light and is open to a screened porch, providing access to the private, fenced back courtyard. New (December 2024) High efficiency RHEEM 15.3 SEER AC unit keeps utility costs lower. New Roof (2021) New 6 panel Front entry door January (2025) New carpet in both bedrooms installed January (2025) Replumbed with New PEX plumbing pipes, New Refrigerator (2025) New light fixtures throughout. As a resident, you'll have access to the community pool and the convenience of being close to Winter Park - Park Avenue, the Cross Seminole Trail and Cady Way Trail, Winter Park Village, UCF and Full Sail. The location offers easy access to major roadways, shopping, and dining and is served by the reputable Seminole County Schools. Complete with fenced back courtyard! Community has swimming pool & bathrooms. ** Exterior of the building is scheduled to be painted. ** Professionally cleaned for new owners. Never smoked in. Compare to others needing all these upgrades.
Listing Agent: Tom Bercini (407-925-4760)
1871 BRYAN AVE, WINTER PARK, FL 32789
$499,0006 Days on yellowkey MLS ID: O6410779
0 Days Off yellowkey (back on 5/27/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1985 Tax: $3,328 (2025)Community: Lakeview TerraceSingle Family
Taxes:$3,328
Remarks: Under contract-accepting backup offers. 1871 Bryan Avenue presents a rare opportunity to own in one of Winter Park’s most desirable pockets without the million-dollar price tag. Located in the heart of 32789 on a 50x127 lot, this charming home offers 1,210 square feet with an efficient layout ideal for a first-time buyer, downsizing homeowner, or investor looking for long-term upside in a prime location. Just minutes from Park Avenue, Winter Park Village, popular restaurants, shopping, and everyday conveniences, the lifestyle and walkability are hard to beat. Major updates include roof (2020), water heater (2026), and HVAC (2009), offering peace of mind for the next owner. Whether you’re looking to move right in, renovate over time, or secure a foothold in the Winter Park market, this property delivers exceptional potential in an unbeatable location.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Jennifer King (407-595-3272)
1581 FOREST AVE, WINTER PARK, FL 32789
$3,393,00081 Days on yellowkey MLS ID: O6382377
REDUCED by $102,000 (2.9%) on 05/21/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4683 Built: 1954 Tax: $20,042 (2024)Community: Ellno WilloSpa: NoSingle Family
Taxes:$20,042
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
927 FAIRWAY DR, WINTER PARK, FL 32792
$680,00045 Days on yellowkey MLS ID: TB8498515
REDUCED by $19,000 (2.7%) on 04/30/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1918 Built: 1973 Tax: $4,784 (2025)Community: Golfside Sec 03Spa: NoSingle Family
Taxes:$4,784
Remarks: Welcome to this beautifully updated home offering the perfect blend of comfort, style and convenience. From the moment you arrive, you’ll notice the inviting tree-lined streets in this quiet residential neighborhood. Step inside to discover a bright, thoughtfully designed layout, filled with natural light, featuring spacious living areas and tasteful updated finishes throughout. The updated, open-concept kitchen is a true centerpiece, complete with modern appliances, ample cabinetry, a generous peninsula, and in eat-in area, ideal for gathering with family and friends. The primary suite provides a relaxing retreat with a recently updated in-suite bathroom and plenty of closet space. Additional bedrooms are generously sized, including a fourth bedroom, perfect for multi-generational living, guests, or a home office. Outside, enjoy a sparkling, screened-enclosed pool, and a private backyard oasis, with plenty of yard space to relax, play, or entertain. Whether you're hosting a weekend barbecue or enjoying a quiet evening, this outdoor space offers endless possibilities. Walk over to the Winter Pines golf course located behind the home, where you can enjoy lunch at the beautifully updated clubhouse, hit the driving range, or enjoy the seasonal community events like Santa in the Park, Movie in the Park, or occasional neighborhood happy hours. Located in the beautiful neighborhood of Winter Park Pines with amenities such as Ward Park, Brookshire Elementary, Winter Park HS, and the Cady Way bike trail, which you can take to Baldwin Park’s main street for shopping and dining, or a stroll around Lake Baldwin. Conveniently located near downtown Orlando, Park Avenue for shopping and dining, or just minutes from the 417 for commuting. Seller offering a home warranty to a buyer for the first year.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
1200 VIA SALERNO, WINTER PARK, FL 32789
$5,995,000108 Days on yellowkey MLS ID: O6381761
REDUCED by $205,000 (3.3%) on 05/07/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5476 Built: 2001 Tax: $40,087 (2024)Community: Cloister Grove SubSpa: NoSingle Family
Taxes:$40,087
Remarks: Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage Venini chandelier immediately sets the tone for the exceptional craftsmanship carried throughout the home. The main gathering room is striking and inviting, defined by vaulted ceilings, a Sequoia leathered stone fireplace hearth, and a wall of glass sliders that open seamlessly to the covered lanai and heated saltwater pool. The connection between indoors and out is effortless, designed for year-round entertaining and relaxed daily living, enhanced by a full outdoor audio system. A light-filled breakfast room sits just off the kitchen, offering an intimate everyday dining space. At the heart of the home, the custom kitchen is a showpiece. Naica leathered stone countertops and a waterfall island are complemented by custom cabinetry extending to the ceiling, a professional-grade appliance suite featuring Sub-Zero and Wolf, and convenience of two Miele dishwashers. Directly adjacent, the pantry mirrors the kitchen’s cabinetry and craftsmanship and features a built-in coffee station, seamlessly connecting to the laundry area and three-car side-entry garage. A beautifully appointed guest powder room with an integrated sink is thoughtfully positioned nearby. A separate lounge showcases a custom wet bar highlighted by dramatic stonework and an integrated sink, an elegant setting for conversation and evening gatherings. A dedicated office positioned just outside the primary suite features a wall of floor-to-ceiling shelving, cabinetry and file drawers. The primary suite serves as a private sanctuary, enhanced by vaulted ceilings, backyard views and a stately two-sided stone fireplace shared with the office. Two custom walk-in closets provide exceptional storage, while the spa-inspired bath showcases Taj Mahal leathered stone countertops with integrated dual sinks, a soaking tub and an oversized glass shower with dual showerheads. Upstairs, four additional bedrooms with custom closets are complemented by beautifully finished baths and a loft sitting area with hallway built-ins. Two of the bedrooms and a bath may be closed off to create a private suite, ideal for guests or multigenerational living. A secondary staircase leads to an impressive media room equipped with a 98-inch television, state-of-the-art 7.1 surround sound and extensive storage. Outdoor living is equally elevated, featuring a weathered marble pool deck, dedicated pool bath, newly installed summer kitchen with Coyote gas grill, hood vent, sink, and leathered stone counters and backsplash, plus an outdoor living room anchored by a two-sided fireplace and television. Modern systems include a Lutron lighting system on the main level, water filtration & softener, ADT alarm - security cameras throughout and a whole-home natural gas generator. Every element of this residence has been newly installed and custom-designed, resulting in a home that blends sophisticated design, advanced functionality, and exceptional spaces for intimate living and grand entertaining. From custom millwork to curated stone selections, this home reflects uncompromising quality and thoughtful design.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
100 S INTERLACHEN AVE #503, WINTER PARK, FL 32789
$879,000264 Days on yellowkey MLS ID: O6343006
2 Days Off yellowkey (back on 5/27/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1143 Built: 1971 Tax: $7,844 (2024)Community: Cloisters CondoCondo
Taxes:$7,844
Remarks: Under contract-accepting backup offers. Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The kitchen features solid wood cabinetry, granite countertops and refined finishes. Both baths are fully updated, including a new tub with glass enclosure in the guest bath and a walk-in shower with frameless glass in the primary suite. Tile flooring, custom vanities and designer fixtures complete each space. Engineered hardwood flooring runs throughout the main living areas, with plush carpet in the bedrooms for added comfort. The primary suite includes custom built-ins, dual closets and a built-in desk with additional cabinetry, delivering elegance and function. The second bedroom offers flexibility as a guest room or study and features optional shared access from the primary suite for additional privacy. Additional highlights include a covered and assigned parking space equipped with one of the building’s few electric vehicle charging stations, ample guest parking and access to a community dock with boat slips available through a resident lottery system. The Cloisters has successfully completed all required Milestone Inspections and the Structural Integrity Reserve Study, ensuring peace of mind for future residents and affirming the association’s commitment to long-term stewardship. Amenities include two fitness centers with dry saunas and a newly renovated clubhouse with kitchen and a partial bath for use as a powder room, ideal for hosting private events. Ideally positioned just steps from the dining, shopping and cultural energy of Park Avenue and in proximity to Rollins College, this original-owner residence offers a compelling blend of lifestyle, location and enduring design.
Listing Agent: Drew Henner (407-406-0662)
1092 EASTBROOK BLVD, WINTER PARK, FL 32792
$399,00016 Days on yellowkey MLS ID: O6407251
REDUCED by $11,000 (2.7%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1122 Built: 1959 Tax: $4,373 (2025)Community: Eastbrook SubSingle Family
Taxes:$4,373
Remarks: Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled, there are new windows, new electric outlets throughout, new light fixtures, roof replaced in 2022,kitchen beautifully redone 2020 with new cabinets and Granite counter tops. Additional upgrades throughout the home include new luxury vinyl flooring, new vanity in master bath, new enhanced pool liner, new robot pool vacuum, new garage door house has been painted inside and out. The location is close to shopping, Costco and other stores also located near by. Full Sale, Rollins College and downtown Winter Park to the west and UCF to the East within close proximity. This is a must see. Owner is realtor.Buyer to verify room measurements.
Listing is courtesy of: JC FLORIDA REALTY LLC (407-257-8265)
Listing Agent: Eva Firios (321-662-1501)
1593 LAWNDALE CIR, WINTER PARK, FL 32792
$480,00017 Days on yellowkey MLS ID: O6402014
REDUCED by $10,000 (2.0%) on 05/27/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1808 Built: 1984Monthly Fee: $49 Tax: $5,010 (2025)Community: Country LaneSpa: NoSingle Family
Taxes:$5,010
Remarks: Beautifully renovated 3 bedroom 2.5 bath pool home located in the lake-centric community of Country Lane in Winter Park. Residents enjoy exclusive access to Lake Florence, offering kayaking, fishing, and scenic outdoor recreation just moments from home. Perfectly positioned on a premium lot with ample space, this property combines privacy, modern upgrades, and exceptional indoor-outdoor living. Recently renovated, the home features brand-new interior paint and a stunning designer kitchen complete with quartz countertops, white shaker cabinetry, and stainless steel appliances. The oversized pool and expansive paver deck create the ideal setting for entertaining, relaxing, and sunbathing year-round. Additional updates include a 2022 roof for added peace of mind. Inside, rich wood flooring flows throughout the home, complemented by soaring ceilings and a cozy fireplace in the family room. The oversized primary suite offers ample space for a king-sized bed, seating area, dresser, and more, while custom built-in closet organizers provide exceptional storage. A secondary upstairs bedroom also features custom closet systems. The screened lanai seamlessly blends indoor and outdoor living and has been thoughtfully upgraded with elegant wood plank ceilings, creating a warm and inviting atmosphere overlooking the pool. Conveniently located with easy access to SR-426 and SR-436, this home is less than five minutes from shopping, dining, entertainment, Trinity Preparatory School, Costco, Target, and vibrant downtown Winter Park.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Daniel Hsieh (813-313-0010)
440 CAMBRIDGE BLVD, WINTER PARK, FL 32789
$380,00025 Days on yellowkey MLS ID: O6403694
1 Days Off yellowkey (back on 5/27/2026)
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 988 Built: 1950 Tax: $4,386 (2025)Community: Glencoe SubSingle Family
Taxes:$4,386
Remarks: Under contract-accepting backup offers. **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.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
621 HUNTINGTON AVE, WINTER PARK, FL 32789
$1,795,00062 Days on yellowkey MLS ID: O6394464
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2399 Built: 2008 Tax: $12,854 (2025)Community: Winter Park RevSpa: NoSingle Family
Taxes:$12,854
Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!
Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)
Listing Agent: Noelle Leblanc (407-491-2744)
1407 MILLER AVE, WINTER PARK, FL 32789
$899,00018 Days on yellowkey MLS ID: O6406408
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1884 Built: 2023Monthly Fee: $200 Tax: $6,818 (2025)Community: H Vanwies SubSingle Family
Taxes:$6,818
Remarks: Experience refined luxury and effortless living at 1407 Miller Avenue, ideally situated in one of Winter Park’s most desirable and walkable enclaves near the NEW Minnesota Row. Built by SGC Homes, this exceptional Modern Mediterranean detached townhome combines timeless architecture with sophisticated contemporary finishes along a charming, tree-lined brick street. Offering 3 bedrooms, 2.5 bathrooms, and 1,884 square feet of thoughtfully designed living space, the residence features a highly sought-after first-floor primary suite and the privacy of only one shared wall at the garage—no shared interior living walls!! Interior highlights include Level 4 drywall finishes, wide-plank engineered oak flooring, Bosch appliances, LED mirrors, and an impressive Hunter Douglas automated shade system. The open-concept floor plan is both functional and inviting, filled with natural light and seamlessly extending to a private paved patio and fenced backyard—ideal for entertaining, quiet outdoor living, or the future addition of a pool or spa. Set within an exclusive four-residence enclave, this low-maintenance property offers a true lock-and-leave lifestyle just minutes from Park Avenue’s premier dining, boutique shopping, Publix, AdventHealth, and everyday conveniences. Additional features include a private two-car garage with EV charging capability and dedicated guest parking. A rare opportunity to own a design-forward residence in the heart of Winter Park.
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Amanda Wood (321-229-8389)
914 ENCLAVE PL, WINTER PARK, FL 32792
$1,895,00073 Days on yellowkey MLS ID: O6391825
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3617 Built: 2026Monthly Fee: $372 Tax: $10,000 (2025)Community: The Enclave Winter ParkSingle Family
Taxes:$10,000
Remarks: Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create a elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
Listing Agent: Matthew Burks (407-257-5347)
926 ENCLAVE PL, WINTER PARK, FL 32792
$2,235,00012 Days on yellowkey MLS ID: O6408030
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4150 Built: 2026Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
Taxes:$9,900
Tax Year: 2026
Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
Listing Agent: Laura Earl (443-994-9441)
910 ENCLAVE PL, WINTER PARK, FL 32792
$1,899,00018 Days on yellowkey MLS ID: O6406803
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3620 Built: 2027Monthly Fee: $124 Tax: $9,900 (2026)Community: The Enclave Winter ParkSingle Family
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