Vintage homes for sale & real estate in Pound Ridge, NY

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ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, NY:
Presenting a Pound Ridge home where timeless historic elegance meets refined modern living. Nestled in the heart of Pound Ridge on a sprawling 9.87 acres, this charming 1835 O'Brien & Kinkel Colonial gem has been lovingly restored and updated to create a seamless blend of vintage charm and modern comfort. The home offers 3 bedrooms, 1.5 bathrooms, gourmet kitchen with a pantry, charming breakfast nook, a cozy fireplace and hardwood floors throughout. Beyond the elegant French doors, you'll find a captivating wraparound wood porch and stone patio, offering panoramic views of the serene backyard complete with your own private pond.

$1,200,000

3 beds1.5 baths1,558 sq ft

100 Salem Rd, Pound Ridge, NY 10576

Breakfast nook • Gourmet kitchen • Private pond

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, NY:
Endless possibilities await - restore, rebuild, or reimagine this serene Pound Ridge property and create the lifestyle you’ve been dreaming of. This remarkable 7-acre property, once home to horses and still featuring the remnants of a paddock and two-stall barn, is nestled near the end of a stonewall-lined driveway. The existing two-bedroom, one-bath residence with an unfinished modern addition (approximately 1,806 sq. ft. ) offers a rare opportunity to own a country retreat. Surrounded by stately oaks, dogwoods, pines, and mountain laurel, the tranquil setting provides privacy, beauty, and space that are increasingly hard to find. The grounds of the property include a non-working ing

$690,000

2 beds1 bath1,806 sq ft

98 Eastwoods Rd, Pound Ridge, NY 10576

7 acre property • Two stall barn • Vaulted ceilings

Listing by Coldwell Banker Realty

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, NY:
Acceptable Offer - Inspections Complete. Hiram Halle Restoration. Charming Mid-19th Century Antique near the historic hamlet owned by the same family for years. Restored by noted philanthropist Hiram Halle in the 1930’s. Fabulous antique features carefully preserved marrying the past with Halle’s vision. Sun-filled spaces with wide plank floors, period millwork, exposed beams and a signature bow window. Living Room and Dining Room with fireplaces. Vintage Kitchen with antique sink and fireplace. Warm and inviting Family Room with door to Office-perfect for remote work. First Floor Bedroom Suite with door to Screened Porch. Four additional Bedrooms include a Primary Bedroom with

$899,000

5 beds3 baths2,303 sq ft

229 Trinity Pass Rd, Pound Ridge, NY 10576

Exposed beams • Antique features • Wide plank floors

Listing by Ginnel Real Estate

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, NY:
Rare lakefront privacy in this charming 1940's vintage home with lakeside pool and almost 3 acres of flat, usable land. A stunning site, bordered by a forever green land preserve, broad lawns and water. The glacier formed lake is crystal clear, attracting an amazing display of birds and wildlife. Fabulous fishing, paddling, swimming, sailing. Not a cottage but a true house, the home is solidly built, typical of the vintage, possessing many period details all combining to charming effect. 3 bedrooms can easily live as 4, or even 5. Also included is a 2-story pool house with storage, deck and finished room upstairs. Ideally located, with the 4700 acre Pound Ridge Reservation only half a mile

$2,350,000

3 beds3 baths3,186 sq ft

93 Cross Pond Rd, Pound Ridge, NY 10576

2.88 acre lot • 2 garage spots • Pool

Listing by William Raveis-New York LLC

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, NY:
Rare Mixed-Use Opportunity. 259 Westchester Avenue is part of Pound Ridge’s rich past. Located in the heart of the historic hamlet, it was the former Samuel Parker house. Built in 1860, this mixed-use building has housed the old Schelling’s Market, as well as the Samuel Parker Café. It currently is home to The Huntress, a high-end design and retail store. Located across the street from Jean George’s Inn at Pound Ridge, this unusual offering enjoys high visibility near the intersection of Routes 124 , 172 and 137. It is situated next to the town-owned Conant Hall and close to the Hiram Halle Library as well as the Pound Ridge Historical Society. The property, a . 27-

$2,695,000

3 beds2.5 baths4,225 sq ft

259 Westchester Ave, Pound Ridge, NY 10576

On-site parking • Historic hamlet • High visibility

Listing by Ginnel Real Estate

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ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, CT:
This property wins BEST-IN-CLASS with brand new renovation, perfectly situated in a prime west-side neighborhood location near New Canaan village. This turnkey home blends modern elegance & timeless charm, offering five bedrooms, four and a half bathrooms, and 3 floors of sophisticated living space on two private, park-like acres. Main floor key features: Gourmet Kitchen: New, classic-modern kitchen featuring double islands, top-tier stainless SubZero & Wolfe appliances, a walk-in pantry, an adjacent sun-filled family room with fireplace, formal dining room, living room with fireplace & access to the wrap-around slate patio. Primary Suite: A spacious addition includes a pr

$2,995,000

5 beds4.5 baths5,731 sq ft

148 W Hills Rd, New Canaan, CT 06840

Private balcony • Three car garage • Gourmet kitchen

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, CT:
Nestled in one of Connecticut's most sought-after estate neighborhoods and just minutes from town, this spectacular 1939 Classic Colonial blends timeless elegance with every modern amenity. Set on nearly 5 bucolic acres of rolling lawns, perennial gardens, and mature trees, this pristine property offers unmatched privacy and beauty. The grand approach includes a stately driveway with a central fountain leading to an inviting paneled foyer. Inside, the gracious living room with fireplace and built-ins opens to a formal dining room that overlooks the magnificent grounds. The chef's kitchen, complete with eat-in area, is perfect for both everyday living and entertaining. Unique lifestyle featu

$5,995,000

6 beds6 baths7,605 sq ft

276 Greenley Rd, New Canaan, CT 06840

Bucolic acres • Central fountain • Perennial gardens

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, NY:
Nestled along one of Bedford’s most scenic and tranquil country lanes and just minutes from the heart of historic Bedford Village, this completely renovated modern farmhouse-inspired home captures the perfect balance of refined luxury, modern comfort, and timeless charm. Reimagined with exceptional attention to detail, the final touches are just being completed. Every element reflects an effortless blend of sophistication, quality craftsmanship, and ease of living. Set on a great lot, the property enjoys expansive lawn areas and water views of a nearby pond. The setting provides quiet surroundings that immerse you in the beauty and serenity of nature. At the heart of the home is a bra

$1,525,000

3 beds2 baths2,167 sq ft

65 Hickory Ln, Bedford, NY 10506

Primary suite • Gourmet kitchen • Completely renovated

Listing by William Raveis-New York LLC

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, CT:
Extraordinary and very rare opportunity to own mixed-use real estate in North Stamford! Grandfathered in as a non-conforming contractors' storage and material yard, this special find offers an adorable 2-bedroom vintage home + a 3-bay garage with 1224 square feet, large doors, high ceilings, deep bays + storage loft which will accommodate 6 vehicles or large scale professional contracting equipment. Possibilities like this in North Stamford are extremely uncommon and offer ideal opportunity for professionals, investors as well as collectors. Property to be sold "As is". Seller requests that buyer erect a 6' fence on the stonewall as part of the purchase offer. Grandfathered docume

$699,000

2 beds1 bath792 sq ft

2856 Long Ridge Rd, Stamford, CT 06903

3-bay garage • Vintage home • Storage loft

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, NY:
Welcome to this traditional farmhouse set on 9 stunning acres—ready to be restored to its former beauty and transformed to suit your vision. This five-bedroom home offers a rare blend of tranquility and versatile living space. The main level features a spacious chef’s kitchen with an eat-in area opening to a warm family room with a fireplace, plus a cozy living room with a second fireplace, a library, full laundry, and a bright sunroom. The second floor includes a large primary bedroom with a double-sided fireplace, updated bath, and balcony overlooking the rolling lawn, along with three additional bedrooms and a finished walk-up attic for storage. The finished lower level&mdash

$1,495,000

5 beds5.5 baths5,687 sq ft

136 Elmwood Rd, South Salem, NY 10590

9.01 acre lot • 4 garage spots • Pool

Listing by Keller Williams Realty Partner

ABOUT THIS HOME
Vintage Home for sale in Pound Ridge, NY:
Discover this charming South Salem farmhouse nestled on two beautiful acres. It features three bedrooms and an open concept chefs kitchen. Enjoy cozy times in front of the fireplace in this warm and inviting ambience. The property offers the perfect blend of country living and modern comfort. With two first floor bedrooms and an open floor plan this home provides ample space for family gatherings and entertaining, while the picturesque acreage offers plenty of room for gardening and outdoor activities. Enjoy serene rural views, a cozy, welcoming atmosphere, and the tranquility of country life minutes from local amenities; only a 12 minute drive to the New Canaan Train Station. An ideal ret

$735,000

3 beds1.5 baths2,085 sq ft

247 Smith Ridge Rd, South Salem, NY 10590

2 acre lot • 2 garage spots • Pool

Listing by William Raveis-New York, LLC

Property at 384 West Ln, Ridgefield, CT 06877, 6 beds, 6 baths

$7,000,000

6 beds6 baths7,541 sq ft

384 West Ln, Ridgefield, CT 06877

Property at 48 Brookwood Ln, New Canaan, CT 06840, 3 beds, 2 baths

$2,950,000

3 beds2 baths1,483 sq ft

48 Brookwood Ln, New Canaan, CT 06840

Property at 2993 High Ridge Rd, Stamford, CT 06903, 2 beds, 1.5 baths

$570,000

2 beds1.5 baths1,359 sq ft

2993 High Ridge Rd, Stamford, CT 06903

Property at 48 Banksville Ave, Bedford, NY 10506, 7 beds, 2 baths

$799,000

7 beds2 baths2,888 sq ft

48 Banksville Ave, Bedford, NY 10506

Listing by Compass Greater NY, LLC

Property at 204 Parade Hill Rd, New Canaan, CT 06840, 4 beds, 4 baths

$2,595,000

4 beds4 baths3,260 sq ft

204 Parade Hill Rd, New Canaan, CT 06840

Property at 1018 North St, Greenwich, CT 06831, 3 beds, 1.5 baths

$999,000

3 beds1.5 baths1,546 sq ft

1018 North St, Greenwich, CT 06831

Property at 27 Wellington Dr, Stamford, CT 06903, 4 beds, 3 baths

$799,999

4 beds3 baths2,402 sq ft

27 Wellington Dr, Stamford, CT 06903

Property at 9 Old Corner Rd, Bedford, NY 10506, 4 beds, 4 baths

$1,995,000

4 beds4 baths3,000 sq ft

9 Old Corner Rd, Bedford, NY 10506

Listing by Ginnel Real Estate

Property at 145 Smith Ridge Rd, South Salem, NY 10590, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths1,924 sq ft

145 Smith Ridge Rd, South Salem, NY 10590

Listing by Ginnel Real Estate

Property at 1196 Route 35, South Salem, NY 10590, 5 beds, 4.5 baths

$1,100,000

5 beds4.5 baths3,648 sq ft

1196 Route 35, South Salem, NY 10590

Listing by Compass Greater NY, LLC

Property at 101 Parade Hill Rd, New Canaan, CT 06840, 3 beds, 2 baths

$1,179,900

3 beds2 baths1,304 sq ft

101 Parade Hill Rd, New Canaan, CT 06840

Property at 565 Oenoke Rdg, New Canaan, CT 06840, 4 beds, 4.5 baths

$4,400,000

4 beds4.5 baths4,927 sq ft

565 Oenoke Rdg, New Canaan, CT 06840

Property at 176 Logan Rd, New Canaan, CT 06840, 5 beds, 3.5 baths

$2,795,000

5 beds3.5 baths4,428 sq ft

176 Logan Rd, New Canaan, CT 06840

Property at 84 Olmstead Ln, Ridgefield, CT 06877, 3 beds, 5.5 baths

$1,750,000

3 beds5.5 baths3,470 sq ft

84 Olmstead Ln, Ridgefield, CT 06877

Houlihan Lawrence Inc.

Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Pound Ridge

There are currently 5 vintage homes for sale in Pound Ridge at a median listing price of $2.27M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Pound Ridge stay on the market for 59 days and receive 1 offers. Popular neighborhoods include North Stamford. This map is refreshed with the newest listings in Pound Ridge every 15 minutes.

In the past month, 3 homes have been sold in Pound Ridge. Find your dream home in Pound Ridge using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Pound Ridge are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Pound Ridge. Our Pound Ridge real estate stats and trends will give you more information about home buying and selling trends in Pound Ridge. If you're looking to sell your home in the Pound Ridge area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Pound Ridge with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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