Location: Orwin Manor Westminster Sec, Winter Park
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1541 WESTCHESTER AVE, WINTER PARK, FL 32789
$1,100,00086 Days on yellowkey MLS ID: O6374409
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2578 Built: 1935 Tax: $5,932 (2024)Community: Orwin Manor Westminster SecSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,932
Elementary School: Killarney Elem
High School: Edgewater High
Tax Year: 2024
Middle School: College Park Middle
Remarks: Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character, modern system updates, and extraordinary future potential. The property offers the unique opportunity to own an estate in a beautifully historic Winter Park neighborhood. Whether thoughtfully renovated, expanded, or reimagined, this property stands as a truly special opportunity in one of Winter Park’s most desirable neighborhoods. A charming brick path leads to a welcoming covered front porch and into a light-filled living room featuring original cypress beams with iron strapping, vaulted ceilings, and a dramatic fireplace crowned by the home’s original bronze chandelier. Glass doors open to a delightful sunroom and a central hallway with abundant storage, and a convenient half bath. The private primary suite is tucked away and offers a peaceful retreat with vaulted ceilings, ceiling fan, wood floors, a wall of closets, and a newly renovated 2023 bath featuring an oversized deep soaking tub and marble vanity. A second ensuite bedroom includes a designer bath with a large glass shower, rain head, and wand. An oversized third bedroom—currently used as a family room—features a vaulted tongue-and-groove ceiling with beams, a walk-in closet, and glass sliders opening to the brick patio and expansive grounds. The dining room and breakfast area flow seamlessly to outdoor living spaces, creating an effortless indoor-outdoor connection. The renovated kitchen includes a farmhouse sink, gas cooking, butcher block countertops, and access to a private walled rose garden and extensive parking options. A newly covered kitchen entrance with custom terrazzo flooring with inset marble pattern leads to a laundry room and versatile studio or workshop with built-ins. Throughout the home, an abundance of windows frames peaceful green views and fills the space with natural light. Outdoors, enjoy raised garden beds, multiple brick patios with fountains, ceiling fans, and partial coverings—perfect for entertaining or quiet reflection. Separate outbuilding is dry, plumbed and wired with a workshop, a large storage space ideal for future ADU and 2-car carport. With major system improvements already completed and an oversized lot offering flexibility for renovation, expansion, new construction, or potential lot division (buyer to verify), this is a legacy property with limitless possibilities. Major system improvements include a 2021 roof & tankless water heater, full re-plumb in 2023, replacement of all major under-home trusses, three updated electrical panels, two HVAC systems (2014 & 2019), providing modern efficiency while preserving the home’s original character. See MLS#O6374414.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Lisa Gould (407-721-7612)
1741 WESTCHESTER AVE, WINTER PARK, FL 32789
$609,900Listed 04/16/2026 4:05PM MLS ID: O6399014
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1434 Built: 1964 Tax: $8,945 (2025)Community: Orwin Manor Westminster SecSingle Family
Taxes:$8,945
Tax Year: 2025
Remarks: Located 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—perfect 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 within a fully fenced backyard ideal for entertaining or relaxing in privacy. Both bathrooms have been tastefully updated, and a new roof installed in 2021 adds to the home’s overall appeal and peace of mind. Ideally positioned just minutes from the 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 that 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.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
1473 BERKSHIRE AVE, WINTER PARK, FL 32789
$1,499,000298 Days on yellowkey MLS ID: O6320741
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2895 Built: 2025 Tax: $5,730 (2024)Community: Orwin Manor Westminster SecSingle Family
Taxes:$5,730
Remarks: One or more photo(s) has been virtually staged. Limited-time incentive: Seller offering a $20,000 buyer credit for qualified buyers. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers the perfect blend of timeless architecture and contemporary design, offering 5 bedrooms, 4 bathrooms, and nearly 2,900 sqft of refined living space. Step inside to discover: • 10-ft ceilings & 8-ft solid-core doors • Wide-plank luxury vinyl flooring throughout • Gourmet kitchen with quartz countertops, custom cabinetry, stainless steel appliances & oversized island • Elegant electric fireplace and expansive great room • Built-in wine cellar discreetly tucked under the stairs • Downstairs guest suite for added privacy Upstairs, the primary suite impresses with pool views and a spa-style bath: dual vanities, soaking tub, walk-in shower, and a generous closet. Three additional bedrooms include a Jack & Jill layout plus one with a private en-suite. A large upstairs laundry room adds convenience. Outside, your private backyard oasis awaits: • In-ground pool, fully landscaped • Summer kitchen with built-in grill • Covered patio for year-round entertaining Located just minutes from Park Avenue, this home offers walkability, top-rated schools, cultural landmarks, boutique shops, and dining. A rare opportunity to own new construction in one of Central Florida’s most iconic neighborhoods. Schedule your private tour today — this home defines the Winter Park lifestyle.
Listing is courtesy of: GOLDEN GROUP REALTY LLC (407-990-5905)
Listing Agent: Milena Fernandes (407-990-5905)
1651 WESTCHESTER AVE, WINTER PARK, FL 32789
$1,449,00013 Days on yellowkey MLS ID: O6384358
0 Days Off yellowkey (back on 4/9/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2426 Built: 1938 Tax: $10,973 (2025)Community: Orwin Manor Westminster SecSingle Family
Taxes:$10,973
Remarks: One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or dedicated laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include a re-roof 2020, HVAC System, Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Shawn Layton (321-514-8055)
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