Woodbury, CT Homes for Sale

Single-Family Homes in Greater Fairfield County

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Single family for sale

105 Old Grassy Hill Road, Woodbury, Connecticut 06798

5Bedroom(s)
4Bathroom(s)
4Parking(s)
7,178Sqft
13Picture(s)
This outstanding private retreat is set on 57+ acres at the end of a cul-de-sac and is bordered by a large pond and the Flanders Nature Center, The property offers beautiful views, hiking trails through the woods and a secluded setting. Custom designed by the architect Moisan, the home features quality details, a gourmet kitchen, and grand entertainment spaces.
$2,800,000

Single family for sale

105 Old Grassy Hill Road, Woodbury, Connecticut 06798
5Bedroom(s)
4Bathroom(s)
4Parking(s)
7,178Sqft
This outstanding private retreat is set on 57+ acres at the end of a cul-de-sac and is bordered by a large pond and the Flanders Nature Center, The property offers beautiful views, hiking trails through the woods and a secluded setting. Custom designed by the architect Moisan, the home features quality details, a gourmet kitchen, and grand entertainment spaces.
$2,800,000

Single family for sale

105 Old Grassy Hill Road, Woodbury, Connecticut 06798
5Bedroom(s)
4Bathroom(s)
$2,800,000

Single family for sale

59 Hillside Road, Woodbury, Connecticut 06798

5Bedroom(s)
5Bathroom(s)
5Parking(s)
14,192Sqft
40Picture(s)
Amazing views and gorgeous surroundings adorn this luxury villa situated on a hillside in historic Woodbury. Enjoy serenity in your remarkable outdoor living space while taking in the miles of rolling hills. Fine details in the construction and finish can be admired throughout the over 9,000 ft² of this dream dwelling "Masterfully" designed by noted Architect Rick Moisan of Moisan Architects.
$1,899,000

Single family for sale

59 Hillside Road, Woodbury, Connecticut 06798
5Bedroom(s)
5Bathroom(s)
5Parking(s)
14,192Sqft
Amazing views and gorgeous surroundings adorn this luxury villa situated on a hillside in historic Woodbury. Enjoy serenity in your remarkable outdoor living space while taking in the miles of rolling hills. Fine details in the construction and finish can be admired throughout the over 9,000 ft² of this dream dwelling "Masterfully" designed by noted Architect Rick Moisan of Moisan Architects.
$1,899,000

Single family for sale

59 Hillside Road, Woodbury, Connecticut 06798
5Bedroom(s)
5Bathroom(s)
$1,899,000

Single family for sale

325 Woodbury Road, Watertown, Connecticut 06795

5Bedroom(s)
4Bathroom(s)
4Parking(s)
7,005Sqft
41Picture(s)
This beautiful Georgian Revival Colonial mansion in Watertown, CT is known as the Lilley House. It was built in 1926 for Theodore Lilley, son of Connecticut Governor George L. Lilley. Situated in the historic area by Taft School, this rare 3.3 acre estate has been meticulous restored and is of significant historic and architectural interest.
$1,350,000

Single family for sale

325 Woodbury Road, Watertown, Connecticut 06795
5Bedroom(s)
4Bathroom(s)
4Parking(s)
7,005Sqft
This beautiful Georgian Revival Colonial mansion in Watertown, CT is known as the Lilley House. It was built in 1926 for Theodore Lilley, son of Connecticut Governor George L. Lilley. Situated in the historic area by Taft School, this rare 3.3 acre estate has been meticulous restored and is of significant historic and architectural interest.
$1,350,000

Single family for sale

325 Woodbury Road, Watertown, Connecticut 06795
5Bedroom(s)
4Bathroom(s)
$1,350,000

Single family for sale

28 Leavenworth Road, Woodbury, Connecticut 06798

3Bedroom(s)
2Bathroom(s)
2Parking(s)
4,734Sqft
41Picture(s)
Set back on 9+ acres, this property offers privacy in a choice location. As visitors ease down its circular stone drive the New England Colonial charm of this exceptional estate welcomes them. Upon entering the formal foyer the homes texture and character are made obvious by the wooden wall cladding, a detail that is carried throughout much of the home.
$1,200,000

Single family for sale

28 Leavenworth Road, Woodbury, Connecticut 06798
3Bedroom(s)
2Bathroom(s)
2Parking(s)
4,734Sqft
Set back on 9+ acres, this property offers privacy in a choice location. As visitors ease down its circular stone drive the New England Colonial charm of this exceptional estate welcomes them. Upon entering the formal foyer the homes texture and character are made obvious by the wooden wall cladding, a detail that is carried throughout much of the home.
$1,200,000

Single family for sale

28 Leavenworth Road, Woodbury, Connecticut 06798
3Bedroom(s)
2Bathroom(s)
$1,200,000

Single family for sale

283 Saw Pit Hill Road, Woodbury, Connecticut 06798

4Bedroom(s)
5Bathroom(s)
5Parking(s)
6,000Sqft
41Picture(s)
An Exceptional Private Retreat awaits on over nine beautiful acres. Extraordinary details throughout with functional living spaces and designed with every luxurious amenity imaginable. Gorgeous wrap around mahogany covered porch (with hot tub). Stunning two-story entry.
$999,000

Single family for sale

283 Saw Pit Hill Road, Woodbury, Connecticut 06798
4Bedroom(s)
5Bathroom(s)
5Parking(s)
6,000Sqft
An Exceptional Private Retreat awaits on over nine beautiful acres. Extraordinary details throughout with functional living spaces and designed with every luxurious amenity imaginable. Gorgeous wrap around mahogany covered porch (with hot tub). Stunning two-story entry.
$999,000

Single family for sale

283 Saw Pit Hill Road, Woodbury, Connecticut 06798
4Bedroom(s)
5Bathroom(s)
$999,000

Single family for sale

32 & 40 Peter Road, Woodbury, Connecticut 06798

5Bedroom(s)
4Bathroom(s)
4Parking(s)
5,087Sqft
24Picture(s)
A quiet piece of paradise awaits you in sought after Litchfield county. This brilliantly designed home includes 2 lots #32 and #40 on over 5 stately acres in Woodbury, CT. Grace and sophistication is brought to life yet is relaxed enough to call a family retreat.
$895,000

Single family for sale

32 & 40 Peter Road, Woodbury, Connecticut 06798
5Bedroom(s)
4Bathroom(s)
4Parking(s)
5,087Sqft
A quiet piece of paradise awaits you in sought after Litchfield county. This brilliantly designed home includes 2 lots #32 and #40 on over 5 stately acres in Woodbury, CT. Grace and sophistication is brought to life yet is relaxed enough to call a family retreat.
$895,000

Single family for sale

32 & 40 Peter Road, Woodbury, Connecticut 06798
5Bedroom(s)
4Bathroom(s)
$895,000

Single family for sale

1 The Estate on Meadowbrook Farm, Woodbury, Connecticut 06798

5Bedroom(s)
3Bathroom(s)
3Parking(s)
5,403Sqft
35Picture(s)
Fall in love with this breath taking property in one of the most charming corners of Connecticut. Exquisite custom built estate surrounded by 400 acres of natural paradise. This fabulous estate is built with state of the art quality components, superior materials and craftsmanship. You simply can not find another property like this so close to Manhattan. This is your ultimate dream home.
$849,000

Single family for sale

1 The Estate on Meadowbrook Farm, Woodbury, Connecticut 06798
5Bedroom(s)
3Bathroom(s)
3Parking(s)
5,403Sqft
Fall in love with this breath taking property in one of the most charming corners of Connecticut. Exquisite custom built estate surrounded by 400 acres of natural paradise. This fabulous estate is built with state of the art quality components, superior materials and craftsmanship. You simply can not find another property like this so close to Manhattan. This is your ultimate dream home.
$849,000

Single family for sale

1 The Estate on Meadowbrook Farm, Woodbury, Connecticut 06798
5Bedroom(s)
3Bathroom(s)
$849,000

Single family for sale

270 Main Street, Woodbury, Connecticut 06798

5Bedroom(s)
2Bathroom(s)
2Parking(s)
3,310Sqft
39Picture(s)
The Noah Benedict House circa 1795 has been a community gathering place for centuries and continues today as an anchor to Woodbury's Antique District. Listed on the National Registry of Historic Homes this incredible antique home has been thoughtfully restored while maintaining and preserving its early architectural details.
$699,000

Single family for sale

270 Main Street, Woodbury, Connecticut 06798
5Bedroom(s)
2Bathroom(s)
2Parking(s)
3,310Sqft
The Noah Benedict House circa 1795 has been a community gathering place for centuries and continues today as an anchor to Woodbury's Antique District. Listed on the National Registry of Historic Homes this incredible antique home has been thoughtfully restored while maintaining and preserving its early architectural details.
$699,000

Single family for sale

270 Main Street, Woodbury, Connecticut 06798
5Bedroom(s)
2Bathroom(s)
$699,000

Single family for sale

100 Cat Swamp Road, Woodbury, Connecticut 06798

3Bedroom(s)
2Bathroom(s)
2Parking(s)
3,780Sqft
34Picture(s)
Gorgeous Reproduction Cape by Rick Moisan Architects, combining the elegance of the past with all the conveniences of new. Located on treasured Cat Swamp Road, set privately on 4.
$699,000

Single family for sale

100 Cat Swamp Road, Woodbury, Connecticut 06798
3Bedroom(s)
2Bathroom(s)
2Parking(s)
3,780Sqft
Gorgeous Reproduction Cape by Rick Moisan Architects, combining the elegance of the past with all the conveniences of new. Located on treasured Cat Swamp Road, set privately on 4.
$699,000

Single family for sale

100 Cat Swamp Road, Woodbury, Connecticut 06798
3Bedroom(s)
2Bathroom(s)
$699,000

Single family for sale

130 Quassuk Road, Woodbury, Connecticut 06798

4Bedroom(s)
2Bathroom(s)
2Parking(s)
4,455Sqft
41Picture(s)
Private gated entry, 6+ acres, with a must-see Pool Paradise! Just 90 mins to NYC, this beautiful 4 bedroom Colonial on over 6 acres of land provides plenty of space for living and playing. The majestic entryway leads to the kitchen featuring stainless appliances and granite countertops. Enjoy a meal at the enormous island, or move to the eat-in area for additional seating.
$639,900

Single family for sale

130 Quassuk Road, Woodbury, Connecticut 06798
4Bedroom(s)
2Bathroom(s)
2Parking(s)
4,455Sqft
Private gated entry, 6+ acres, with a must-see Pool Paradise! Just 90 mins to NYC, this beautiful 4 bedroom Colonial on over 6 acres of land provides plenty of space for living and playing. The majestic entryway leads to the kitchen featuring stainless appliances and granite countertops. Enjoy a meal at the enormous island, or move to the eat-in area for additional seating.
$639,900

Single family for sale

130 Quassuk Road, Woodbury, Connecticut 06798
4Bedroom(s)
2Bathroom(s)
$639,900

Single family for sale

89 Quail Run Road, Woodbury, Connecticut 06798

3Bedroom(s)
3Bathroom(s)
3Parking(s)
2,650Sqft
15Picture(s)
Quality to-be-built custom Eyebrow Colonial by HOBI award winning builder Connecticut Residential on lot with breathtaking VIEWS for miles! This exceptional ENERGY STAR CERTIFIED home on a quiet cul-de-sac boasts a spacious open floor plan with a wall of windows to drink in the incredible VIEWS! Gorgeous kitchen with granite or quartz countertops, stainless steel appliances, sliders to deck, dini
$635,000

Single family for sale

89 Quail Run Road, Woodbury, Connecticut 06798
3Bedroom(s)
3Bathroom(s)
3Parking(s)
2,650Sqft
Quality to-be-built custom Eyebrow Colonial by HOBI award winning builder Connecticut Residential on lot with breathtaking VIEWS for miles! This exceptional ENERGY STAR CERTIFIED home on a quiet cul-de-sac boasts a spacious open floor plan with a wall of windows to drink in the incredible VIEWS! Gorgeous kitchen with granite or quartz countertops, stainless steel appliances, sliders to deck, dini
$635,000

Single family for sale

89 Quail Run Road, Woodbury, Connecticut 06798
3Bedroom(s)
3Bathroom(s)
$635,000

Single family for sale

17 Transylvania Road, Woodbury, Connecticut 06798

3Bedroom(s)
2Bathroom(s)
2Parking(s)
3,928Sqft
33Picture(s)
Enjoy pure privacy in this turnkey colonial, beautifully sited on 2 acres in Woodbury. Set back down a winding driveway, this immaculate 3 bedroom/2.5 bath home sits among soaring white pines and lush, mature gardens.
$629,000

Single family for sale

17 Transylvania Road, Woodbury, Connecticut 06798
3Bedroom(s)
2Bathroom(s)
2Parking(s)
3,928Sqft
Enjoy pure privacy in this turnkey colonial, beautifully sited on 2 acres in Woodbury. Set back down a winding driveway, this immaculate 3 bedroom/2.5 bath home sits among soaring white pines and lush, mature gardens.
$629,000

Single family for sale

17 Transylvania Road, Woodbury, Connecticut 06798
3Bedroom(s)
2Bathroom(s)
$629,000
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