Homes with Pools for Sale in Woodbury, CT

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ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private setting with a picturesque waterfall nearby for a relaxing stroll, yet you can walk to an amazing collection of local favorites-inc. 9 fine restaurants, 4 diners, a brewery and a pub w/ live entertainment, and a French bakery. No wonder they call it "Food-bury!" Come home by the stone path leading to a beautiful stone landing. Step inside, where warmth & character surround you, the spacious L-shaped living room offers two inviting gathering areas. At one end, a wood-burning fireplace creates a cozy setting w

$875,000

3 beds2.5 baths2,480 sq ft

2 Pomperaug Rd, Woodbury, CT 06798

Stone path • High-end appliances • Soaking tub

OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen, new flooring, and central air. Inside you'll find an open floor plan perfect for entertaining - the kitchen has been completely redesigned featuring new cabinets, quartz countertops, and stainless steel appliances. The modern flooring flows from the kitchen to the fireplace, offering a perfect place for family gatherings. Around the corner you'll find two bedrooms and 1 full bath - the bathroom has been updated and modernized featuring a brand new vanity and tiled shower. The slider door leads to a private patio which is

$199,900

2 beds1 bath913 sq ft

229 Bacon Pond Rd #312, Woodbury, CT 06798

Open floor plan • Quartz countertops • New kitchen

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Set well back from Weekeepeemee Road in one of Woodbury's finest locations, this exceptionally well-built Colonial offers approximately 5,900 square feet of thoughtfully designed living space. Multiple bedroom suites and an open floor plan provide room for everyone, with inviting spaces for both everyday living and entertaining. The beautiful kitchen opens to a covered porch overlooking an expansive patio and gunite pool, creating a seamless connection between indoor and outdoor gatherings. Car enthusiasts will appreciate the remarkable garage and barn space. An attached, heated three-car garage is complemented by a lower-level garage with room for several additional vehicles. An impressive

$2,149,900

5 beds4.5 baths5,973 sq ft

348 Weekeepeemee Rd, Woodbury, CT 06798

Covered porch • Gunite pool • Remarkable garage

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
A Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful country living meets the charm of Woodbury! Set on approximately 9.47 acres, this 3-bedroom, 3-bath home offers an incredible combination of space, privacy, and outdoor living. Surrounded by beautiful natural scenery, the expansive property provides plenty of room to spread out, explore, garden, entertain, or simply enjoy the peaceful setting. Spend warm summer days relaxing by the pool, host gatherings with family and friends, or unwind and take in the privacy of your own country retreat. Inside, the home offers a comfortable and inviting layout with three bedrooms and three full baths, providing plenty o

$850,000

4 beds2.5 baths2,568 sq ft

69 Nonnewaug Rd, Woodbury, CT 06798

Historic appeal • Outdoor living • 9.47 acre lot

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Step inside this wonderful center-hall Colonial and discover a home that is far more inviting than the curb suggests. Built when homes were designed for gracious, comfortable living, it feels elegant yet relaxed, filled with color and thoughtful character. The beautifully crafted floor plan offers intimate parlors, three fireplaces, a generous kitchen, spacious living and dining areas made for gathering, charming Dutch doors, a cozy den, well-proportioned bedrooms, and an exceptional laundry room conveniently located on the same level as the recreation room with its own fireplace. Outdoors, a pool, professionally designed gardens, a growing room, and welcoming terraces create a setting to b

$1,150,000

4 beds4 baths3,968 sq ft

90 Sage Rd, Woodbury, CT 06798

4 acre lot • 2 garage spots • Pool

Property at 241 Hoop Pole Hill Rd, Woodbury, CT 06798, 3 beds, 2.5 baths

$399,000

3 beds2.5 baths2,032 sq ft

241 Hoop Pole Hill Rd, Woodbury, CT 06798

Property at 229 Bacon Pond Rd #313, Woodbury, CT 06798, 2 beds, 1 bath

$209,900

2 beds1 bath913 sq ft

229 Bacon Pond Rd #313, Woodbury, CT 06798

Property at 8 Woods Way #8, Woodbury, CT 06798, 3 beds, 2.5 baths

$299,000

3 beds2.5 baths1,467 sq ft

8 Woods Way #8, Woodbury, CT 06798

Property at 17 Woodbury Hl #17, Woodbury, CT 06798, 2 beds, 2.5 baths

$527,900

2 beds2.5 baths1,673 sq ft

17 Woodbury Hl #17, Woodbury, CT 06798

Property at 40 Ruffin Rd, Woodbury, CT 06798, 4 beds, 2.5 baths

$1,590,000

4 beds2.5 baths2,732 sq ft

40 Ruffin Rd, Woodbury, CT 06798

Property at 92 Minortown Rd, Woodbury, CT 06798, 3 beds, 2 baths

$775,000

3 beds2 baths2,448 sq ft

92 Minortown Rd, Woodbury, CT 06798

Property at 35 Woodbury Hl #35, Woodbury, CT 06798, 2 beds, 2.5 baths

$510,000

2 beds2.5 baths1,796 sq ft

35 Woodbury Hl #35, Woodbury, CT 06798

Property at 920 Main St S, Woodbury, CT 06798, 4 beds, 5 baths

$2,995,000

4 beds5 baths5,316 sq ft

920 Main St S, Woodbury, CT 06798

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ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Welcome to a peaceful setting in Heritage Village. This Berkshire-style unit sits beside a tranquil pond, giving you a calm, natural backdrop right outside your door. The large patio is a great spot for morning coffee, evening dinners outside, or simply watching the water and the seasons change. Daily life is easy here. A flat, level walk from the garage means no stairs or hills to manage when you bring in groceries or come home from errands. This unit is ready for your vision. Bring your design ideas and turn it into your own personal oasis, with finishes and style chosen by you, in one of the area's best locations within the community. As part of Heritage Village, you'll also enjoy everyt

$380,000

3 beds2 baths1,716 sq ft

491 Heritage Vlg Unit B, Southbury, CT 06488

Flat level walk • Large patio • Tranquil pond

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Nothing to do but move-in to this gorgeous remodeled "Carriage House" in 55+ Heritage Village! Lovely hardwood floors in the LR/DR, kitchen, hall and bedroom. The kitchen has been opened to the dining area and includes white cabinets, granite counters and stainless-steel appliances. The living room offers a charming window seat, wood burning fireplace and sliders to the deck. The bedroom is next to the stunning remodeled bathroom which walk-in shower and stylish vanity and fixtures. All this in the desirable Winship neighborhood near the gardens!

$230,000

1 bed1 bath928 sq ft

533 Heritage Vlg Unit B, Southbury, CT 06488

White cabinets • Granite counters • Hardwood floors

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Some kids have Disney World, 55+ have HERITAGE VILLAGE! Resort like daily living is waiting for you at #522B! Renovated down to the studs 2 Bdrm/2 bath level RANCH unit w/ NO STEPS!. Newer Rich bamboo flooring; SAMSUNG S/S appl; WOOD BURNING Fireplace; 2 spacious updated/tiled bathrooms; mirrored dual closet dressing room; spacious open floor plan; kitchen offers extra corner versatile space currently used as office. New Hot Water heater tank. Not a boring white/gray unit, but filled w/ unique characteristics and warmth, worthy of its COUNTRY HOME model name. 18 hole championship golf course intertwines thru the HV homes- 1 of 3 courses! 4 pools (incl Saltwater), Tennis, Bocci, Pickleball,

$375,000

2 beds2 baths1,398 sq ft

522 Heritage Vlg Unit B, Southbury, CT 06488

4 pools • $775 HOA • Garage

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
A PRIVATE BACKYARD OASIS AWAITS AT 49 DEERWOOD DRIVE. Set on a level, beautifully landscaped property, this inviting home offers an exceptional blend of classic character, comfortable living, and resort-like outdoor enjoyment. Mature gardens and landscaping surround the patio, charming gazebo, and in-ground pool, creating a truly special setting for summer gatherings, quiet mornings, and effortless entertaining. Inside, warm oak floors and thoughtful details add timeless appeal. The living room features a gas fireplace, while the family room is anchored by a wood-burning fireplace surrounded by built-ins and bookshelves, with sliders opening directly to the rear yard. Pocket doors add an el

$725,000

4 beds3 baths2,890 sq ft

49 Deerwood Dr, Bethlehem, CT 06751

Mature gardens • In-ground pool • Charming gazebo

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive Colonial-Contemporary residence offers an exceptional combination of privacy, natural beauty, and modern comfort on nearly 10 acres. Surrounded by mature trees, lush landscaping, and vibrant plantings, the property enjoys a peaceful, secluded setting with the gentle sounds of Transylvania Brook flowing just beyond the backyard. A long, paved, beautifully illuminated driveway leads to the home, where an impressive double-door entrance welcomes you into a spacious foyer featuring a unique indoor water feature. The thoughtful

$1,149,000

3 beds2.5 baths4,012 sq ft

24 Roxbury Rd, Woodbury, CT 06798

Indoor water feature • Fenced yard • Nearly 10 acres

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Woodbury, CT:
Classic Colonial Set on 17+ High Pastoral Acres in Southern Roxbury CT. New Heated Gunite Pool Expertly Sighted Amongst Flowing Pasture & Attractive Outbuildings. 4 Bedroom, 2 Full + 2 Partial Bath Main Residence & Large Multi-Stall Horse Barn with 1 Bed/1 Bath Apt Above. Separate Large 3-Bay Utility Garage Plus Multiple Other Storage Sheds. Wonderful Floorplan Includes Private Living Room with Fireplace; a Welcoming Eat-in Kitchen, Dining Room & an Inviting Family Room with Beamed Ceiling & Access to Large Deck. Several Bonus Rooms Include: a Main Level Study, Lower Level Offices, Gym & Rec Room. An Attached 2-Car Garage Makes for Practical Country Living. Sev

$1,595,000

4 beds3 baths4,310 sq ft

25 Highmeadow Ln, Roxbury, CT 06783

Inviting family room • Private living room • Eat-in kitchen

Property at 496 Heritage Vlg Unit A, Southbury, CT 06488, 2 beds, 2 baths

$259,000

2 beds2 baths1,076 sq ft

496 Heritage Vlg Unit A, Southbury, CT 06488

Property at 626 Heritage Vlg Unit B, Southbury, CT 06488, 2 beds, 2 baths

$289,000

2 beds2 baths1,432 sq ft

626 Heritage Vlg Unit B, Southbury, CT 06488

Property at 616 Heritage Vlg Unit B, Southbury, CT 06488, 2 beds, 2 baths

$375,000

2 beds2 baths1,398 sq ft

616 Heritage Vlg Unit B, Southbury, CT 06488

Property at 126 Bucks Hill Rd, Southbury, CT 06488, 4 beds, 2.5 baths

$999,000

4 beds2.5 baths2,404 sq ft

126 Bucks Hill Rd, Southbury, CT 06488

Property at 63 W Mountain Rd, Washington Depot, CT 06793, 4 beds, 4.5 baths

$2,495,000

4 beds4.5 baths3,699 sq ft

63 W Mountain Rd, Washington Depot, CT 06793

Property at 469 Heritage Vlg Unit A, Southbury, CT 06488, 2 beds, 2 baths

$164,000

2 beds2 baths1,032 sq ft

469 Heritage Vlg Unit A, Southbury, CT 06488

Property at 509 Heritage Vlg Unit B, Southbury, CT 06488, 2 beds, 2 baths

$419,000

2 beds2 baths1,398 sq ft

509 Heritage Vlg Unit B, Southbury, CT 06488

Property at 620 Heritage Vlg Unit B, Southbury, CT 06488, 2 beds, 2 baths

$305,000

2 beds2 baths1,432 sq ft

620 Heritage Vlg Unit B, Southbury, CT 06488

Property at 126 Sunset Rdg, Southbury, CT 06488, 4 beds, 3.5 baths

$1,180,000

4 beds3.5 baths6,183 sq ft

126 Sunset Rdg, Southbury, CT 06488

Property at 517 Heritage Vlg Unit C, Southbury, CT 06488, 2 beds, 2 baths

$199,900

2 beds2 baths1,044 sq ft

517 Heritage Vlg Unit C, Southbury, CT 06488

Property at 35 Schoolhouse Rd, Roxbury, CT 06783, 4 beds, 4.5 baths

$3,250,000

4 beds4.5 baths4,456 sq ft

35 Schoolhouse Rd, Roxbury, CT 06783

Property at 485 Heritage Vlg Unit A, Southbury, CT 06488, 1 bed, 1 bath

$219,900

1 bed1 bath928 sq ft

485 Heritage Vlg Unit A, Southbury, CT 06488

Property at 469 Heritage Vlg Unit B, Southbury, CT 06488, 2 beds, 2 baths

$199,000

2 beds2 baths1,032 sq ft

469 Heritage Vlg Unit B, Southbury, CT 06488

Property at 35 Nettleton Hollow Rd, Bethlehem, CT 06751, 4 beds, 3 baths

$775,000

4 beds3 baths3,020 sq ft

35 Nettleton Hollow Rd, Bethlehem, CT 06751

Homes with Pools for Sale in Woodbury

There are currently 13 homes with pools for sale in Woodbury at a median listing price of $675K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Woodbury stay on the market for 51 days and receive 1 offers. This map is refreshed with the newest listings in Woodbury every 15 minutes.

In the past month, 10 homes have been sold in Woodbury. In addition to houses in Woodbury, there were also 19 condos, 0 townhouses, and 1 multi-family unit for sale in Woodbury last month. Find your dream home in Woodbury 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 Woodbury are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Woodbury. If you're looking to sell your home in the Woodbury area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Woodbury with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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