Moving to Woodbury CT | real estate for sale in Woodbury Connecticut | Property Statistics of living in Woodbury
Woodbury combines historic charm with a strong residential market characterized by attractive neighborhoods, country properties, and upscale homes. The town's location along Route 6 and proximity to Fairfield County enhance its appeal. Property values benefit from sustained demand among buyers seeking a blend of rural character and accessibility. Strong community amenities and architectural preservation contribute to long-term market strength.
62 Heritage Drive
Woodbury, Connecticut 06798
$799,900 | Under Contract - Continue
4 Beds | 3 Baths | 3223 Sqft | 1.25 Acres | 18 Days on Market
Property Type: Single Family For Sale
Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodburys most desirable locations. Just two streets from Woodburys nationally recognized Main Street, this home offers the perfect combination of modern updates, comfortable living, and except...
106 Sprain Brook Road
Woodbury, Connecticut 06798
$550,000 | Active
3 Beds | 2 Baths | 2002 Sqft | 2.77 Acres | 3 Days on Market
Property Type: Single Family For Sale
Welcome home to this charming farmhouse setting with privacy and room to grow. The open flat acreage boasts a 2 stall barn with power ready for a hobby farm, or reimagined as a potential pool house, art studio or potential guest quarters. The 3 bedroom 2 full bath home is set ove...
6 Easy Street
Woodbury, Connecticut 06798
$269,000 | Active
3 Beds | 2 Baths | 1562 Sqft | 0.72 Acres | 14 Days on Market
Property Type: Single Family For Sale
** INVESTORS TAKE NOTICE! ** Nestled in the desirable town of Woodbury, this 3 bedroom, 1.5 bath Colonial presents a unique opportunity to restore and reimagine a property full of charm and potential. Featuring hardwood flooring throughout the majority, spacious interiors, newer ...
18 South Street
Woodbury, Connecticut 06798
$495,000 | Active
4 Beds | 3 Baths | 2880 Sqft | 2.71 Acres | 5 Days on Market
Property Type: Single Family For Sale
Sited privately on 2.7 scenic acres in Woodburys desirable Cardinal Hill neighborhood, this classic four-bedroom Colonial offers a perfect blend of quiet country living and everyday functionality. As part of a low-fee, self-managed neighborhood association, residents enjoy a wond...
96 Quail Run Road
Woodbury, Connecticut 06798
$895,000 | Active
4 Beds | 3 Baths | 2400 Sqft | 1.28 Acres | 6 Days on Market
Property Type: Single Family For Sale
QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBUR...
94 Quail Run Road
Woodbury, Connecticut 06798
$645,000 | Under Contract - Continue
3 Beds | 3 Baths | 2081 Sqft | 1.46 Acres | 77 Days on Market
Property Type: Single Family For Sale
QUAIL RUN On the cul de sac - 4 NEW HOMES ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - ...
206 Minortown Road
Woodbury, Connecticut 06798
$575,000 | Active
3 Beds | 3 Baths | 1692 Sqft | 1.14 Acres | 6 Days on Market
Property Type: Single Family For Sale
Cute as a button Cape Cod style home in charming and historic Woodbury! A lovingly cared for home within a short drive of main street, area schools, Walker Road Winery and all other major conveniences. Step right into this light and bright home that provides a newly remodeled kit...
46 Grassy Hill Road
Woodbury, Connecticut 06798
$1,500,000 | Under Contract - Continue
4 Beds | 4 Baths | 3480 Sqft | 3.5 Acres | 11 Days on Market
Property Type: Single Family For Sale
Beautifully updated and impeccably maintained, this custom Colonial offers timeless New England charm in a private setting with gorgeous views of a picturesque waterfall and babbling brook. Set on beautifully landscaped grounds with an additional lot included, the home features w...
17 Carriage Lane
Woodbury, Connecticut 06798
$774,900 | Under Contract - Continue
5 Beds | 4 Baths | 3607 Sqft | 1.01 Acres | 75 Days on Market
Property Type: Single Family For Sale
Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel ...
33 Hurds Hill Road
Woodbury, Connecticut 06798
$525,000 | Active
5 Beds | 3 Baths | 4130 Sqft | 1.46 Acres | 29 Days on Market
Property Type: Single Family For Sale
Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious li...
16 Cross Brook Road
Woodbury, Connecticut 06798
$649,900 | Under Contract - Continue
3 Beds | 2 Baths | 1750 Sqft | 5.51 Acres | 54 Days on Market
Property Type: Single Family For Sale
Fantastic Potential in this home. Three bedroom Cape Cod sitting on 5.50 acre lot with a giant barn that has great potential living space to convert into an in-laws set up, office, studio space or music studio to fit your lifestyle. Home freshly painted interior and exterior. Ren...
241 Hoop Pole Hill Road
Woodbury, Connecticut 06798
$459,000 | Active
3 Beds | 3 Baths | 2032 Sqft | 1.51 Acres | 17 Days on Market
Property Type: Single Family For Sale
Nestled in the highly desirable town of Woodbury, this charming Cape offers just over 2,000 square feet of comfortable living space with endless potential. The home features 3 bedrooms, 2.5 bathrooms, and beautiful hardwood floors throughout. A dedicated home office with custom b...
8 Curtiss Meadows
Woodbury, Connecticut 06798
$874,900 | Active
4 Beds | 5 Baths | 3865 Sqft | 3.12 Acres | 71 Days on Market
Property Type: Single Family For Sale
Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience,...
38 Mountain Road
Woodbury, Connecticut 06798
$494,000 | Under Contract - Continue
3 Beds | 3 Baths | 1704 Sqft | 0.82 Acres | 56 Days on Market
Property Type: Single Family For Sale
Welcome to 38 Mountain Road, a perfect blend of functional living space and privacy while still offering a close proximity to town. Upon entering you are greeted with a warm and welcoming living room. This space flows into the dining room which is right next to the remodeled kitc...
12 Walker Road
Woodbury, Connecticut 06798
$499,989 | Under Contract - Continue
3 Beds | 3 Baths | 1580 Sqft | 1.95 Acres | 31 Days on Market
Property Type: Single Family For Sale
Would you like to live in beautiful Woodbury Connecticut. Set on 1.95 acres of peaceful, private grounds, this beautifully updated 3-bedroom, 2.1-bath home sits gracefully on a gentle rise at the top of the driveway, partially framed by classic white post and rail fencing that en...
49 Scuppo Road
Woodbury, Connecticut 06798
$540,000 | Under Contract - Continue
3 Beds | 2 Baths | 2292 Sqft | 1.1 Acres | 92 Days on Market
Property Type: Single Family For Sale
Discover this beautifully updated ranch-style home ideally situated on over an acre of level, private land. Offering 2292 square feet of comfortable one-level living space, this 3-bedroom, 1.5 bath home combines timeless character with modern upgrades-perfect for those seeking sp...
76 Cowles Road
Woodbury, Connecticut 06798
$1,800,000 | Under Contract
3 Beds | 3 Baths | 2072 Sqft | 40 Acres | 58 Days on Market
Property Type: Single Family For Sale
Rare opportunity to own a spectacular 40-acre estate designed for exceptional horse care, training, and country living-while also offering the flexibility to create a private escape tucked away from it all. This remarkable property features a 150 x 80 indoor riding arena with exc...
27 Middle Quarter Road
Woodbury, Connecticut 06798
$999,900 | Under Contract - Continue
3 Beds | 3 Baths | 2042 Sqft | 1.49 Acres | 193 Days on Market
Property Type: Single Family For Sale
Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The...
20 Stagecoach Road
Woodbury, Connecticut 06798
$629,000 | Under Contract - Continue
4 Beds | 3 Baths | 2157 Sqft | 1.38 Acres | 25 Days on Market
Property Type: Single Family For Sale
Summer opportunity in a highly sought-after neighborhood featuring a private inground pool and backyard retreat. This one checks all the boxes-from cul-de-sac living to privacy and a great setting. Spacious 4-bedroom Colonial with hardwood floors, fireplace, and a partially finis...
61 Silver Brook Lane
Woodbury, Connecticut 06798
$1,069,900 | Under Contract
4 Beds | 4 Baths | 4776 Sqft | 2.3 Acres | 20 Days on Market
Property Type: Single Family For Sale
Exceptional Colonial in one of Woodburys finest developments, beautifully set among similar distinguished homes at the end of Silver Brook Lane. Thoughtfully updated over the past five years with high-quality materials and careful attention to detail, this 4,000+ square foot resi...
48 Coach Light Drive
Woodbury, Connecticut 06798
$1,599,000 | Under Contract
4 Beds | 5 Baths | 5216 Sqft | 4.71 Acres | 40 Days on Market
Property Type: Single Family For Sale
Gloriously Peaceful, Private, Magnificent views...This exceptional residence among similar spectacular homes welcomes you with a dramatic two-story entry - designed for both refined entertaining and comfortable living. The heart of the home is a beautifully appointed chefs kitche...
34 Transylvania Road
Woodbury, Connecticut 06798
$479,900 | Under Contract
3 Beds | 3 Baths | 2016 Sqft | 3 Acres | 256 Days on Market
Property Type: Single Family For Sale
Price Improvement for this Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy th...
338 Good Hill Road
Woodbury, Connecticut 06798
$569,900 | Under Contract - Continue
4 Beds | 2 Baths | 1875 Sqft | 1.53 Acres | 32 Days on Market
Property Type: Single Family For Sale
Nestled on 1.53 acres and set back from the road, this charming Cape Cod style home offers the perfect blend of comfort, character and New England charm. The interior features 2 bedrooms and a full bath on the main and upper level. An inviting Living Room showcases a fireplace wi...
30 Park Road
Woodbury, Connecticut 06798
$650,000 | Active
3 Beds | 4 Baths | 2479 Sqft | 1.34 Acres | 22 Days on Market
Property Type: Single Family For Sale
Charming in-town Gambrel Colonial with views of Orenaug Pond, located just up the road from the South Green. Surrounded by historic landmarks such as King Solomons Lodge, the Hurd House, the Glebe House, and other notable properties, this home offers three bedrooms, three full ba...
40 Ruffin Road
Woodbury, Connecticut 06798
$1,900,000 | Active
4 Beds | 3 Baths | 2732 Sqft | 6.3 Acres | 26 Days on Market
Property Type: Single Family For Sale
Its rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, ingroun...
437 Middle Road Turnpike
Woodbury, Connecticut 06798
$545,000 | Active
3 Beds | 2 Baths | 1144 Sqft | 1.43 Acres | 69 Days on Market
Property Type: Single Family For Sale
Everything has already been done for you. Just move in, unpack, and enjoy the ease of single-floor living in this beautifully renovated ranch with endless potential below. Completely renovated and truly move-in ready, this home offers effortless living with every major updated al...
92 Minortown Road
Woodbury, Connecticut 06798
$849,000 | Active
3 Beds | 2 Baths | 2448 Sqft | 5.76 Acres | 28 Days on Market
Property Type: Single Family For Sale
Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on ...
1917 North Main Street
Woodbury, Connecticut 06798
$865,000 | Active
4 Beds | 2 Baths | 4819 Sqft | 5.91 Acres | 29 Days on Market
Property Type: Single Family For Sale
Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28 x 53 post and beam barn with ...
920 South Main Street
Woodbury, Connecticut 06798
$2,995,000 | Active
4 Beds | 6 Baths | 5316 Sqft | 18.23 Acres | 32 Days on Market
Property Type: Single Family For Sale
Warrens Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impr...
207 Grassy Hill Road
Woodbury, Connecticut 06798
$599,000 | Under Contract - Continue
3 Beds | 2 Baths | 1844 Sqft | 2.08 Acres | 39 Days on Market
Property Type: Single Family For Sale
Nestled on a picturesque 2+ acre park-like setting, this beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and natural beauty-with the ease of one-level living. Designed with both style and functionality in mind, the sun-filled open layout ...
439 Washington Road
Woodbury, Connecticut 06798
$289,000 | Active
2 Beds | 2 Baths | 1920 Sqft | 9.88 Acres | 498 Days on Market
Property Type: Single Family For Sale
Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. ...
134 Old Sherman Hill Road
Woodbury, Connecticut 06798
$389,900 | Under Contract
3 Beds | 2 Baths | 1578 Sqft | 0.96 Acres | 2 Days on Market
Property Type: Single Family For Sale
Welcome home to this charming 3-bedroom, 2-bath ranch, perfectly situated on a lovely lot. This home offers comfortable one-level living with a bright and inviting floor plan designed for everyday living and entertaining. The spacious living areas flow seamlessly into the kitchen...
104 Hard Hill Road
Woodbury, Connecticut 06798
$425,000 | Under Contract - Continue
3 Beds | 1 Baths | 1364 Sqft | 1.02 Acres | 49 Days on Market
Property Type: Single Family For Sale
Nestled along a country road on a cul-de-sac, this charming home offers the perfect blend of warmth, comfort, and convenience. A welcoming entry greets you with soaring ceilings, wood floors, and a propane stove that adds both character and cozy ambiance. The spacious country kit...
55 Good Hill Road
Woodbury, Connecticut 06798
$1,995,000 | Active
4 Beds | 5 Baths | 3324 Sqft | 3.67 Acres | 164 Days on Market
Property Type: Single Family For Sale
Step into History with Modern Comfort Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with todays mode...
28 School Street
Woodbury, Connecticut 06798
$775,000 | Active
4 Beds | 4 Baths | 2708 Sqft | 1.41 Acres | 46 Days on Market
Property Type: Single Family For Sale
The Orton-Martin Homestead. One of Woodburys oldest homes has been updated for todays lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden deligh...
5 Westwood Road
Woodbury, Connecticut 06798
$575,000 | Under Contract
3 Beds | 2 Baths | 1961 Sqft | 0.62 Acres | 8 Days on Market
Property Type: Single Family For Sale
Classic early-1900s colonial in the heart of Woodbury with 3 bedrooms, 2 full baths, and over 1,900 square feet of living space. The home offers a comfortable mix of older-home character and practical updates, with hardwood floors, good natural light, and a layout that works well...
89 Lighthouse Road
Woodbury, Connecticut 06798
$450,000 | Under Contract - Continue
3 Beds | 3 Baths | 1210 Sqft | 4.99 Acres | 61 Days on Market
Property Type: Single Family For Sale
** Multiple offers highest and best 5/17 5pm**Tucked away on 4.99 serene wooded acres in picturesque Woodbury, this solidly built Cape Cod offers privacy, charm, and endless potential. Surrounded by mature trees and peaceful natural beauty, the property provides a true country se...
253 Bacon Pond Road
Woodbury, Connecticut 06798
$895,000 | Active
4 Beds | 3 Baths | 2283 Sqft | 3.19 Acres | 61 Days on Market
Property Type: Single Family For Sale
Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, fe...
86 Quail Run Road
Woodbury, Connecticut 06798
$745,000 | Active
3 Beds | 3 Baths | 2060 Sqft | 1.24 Acres | 77 Days on Market
Property Type: Single Family For Sale
QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBUR...
30 Hollow Road
Woodbury, Connecticut 06798
$1,495,000 | Active
5 Beds | 5 Baths | 4884 Sqft | 2.24 Acres | 83 Days on Market
Property Type: Single Family For Sale
Step through the doors of history and into one of Connecticuts most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with...
819 North Main Street
Woodbury, Connecticut 06798
$1,675,000 | Active
3 Beds | 3 Baths | 2992 Sqft | 9.88 Acres | 245 Days on Market
Property Type: Single Family For Sale
Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room,...
339 South Main Street
Woodbury, Connecticut 06798
$874,900 | Active
4 Beds | 3 Baths | 3700 Sqft | 1.39 Acres | 96 Days on Market
Property Type: Single Family For Sale
One of Woodburys last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts...
557 Upper Grassy Hill Road
Woodbury, Connecticut 06798
$895,000 | Active
4 Beds | 4 Baths | 3784 Sqft | 2.73 Acres | 104 Days on Market
Property Type: Single Family For Sale
Welcome to Upper Grassy Hill Living!...
110 Brushy Hill Road
Woodbury, Connecticut 06798
$499,999 | Active
3 Beds | 3 Baths | 2100 Sqft | 1.01 Acres | 108 Days on Market
Property Type: Single Family For Sale
Experience the charm of this classic Cape Cod style property, featuring 3 bedrooms and 2 cozy fireplaces that invite warm gatherings on 1 acre of land perfect for outdoor enjoyment. This country eclectic home blends timeless architecture with modern comfort, offering a serene ret...
19 Hillview Lane
Woodbury, Connecticut 06798
$749,000 | Under Contract - Continue
3 Beds | 4 Baths | 3749 Sqft | 0.74 Acres | 190 Days on Market
Property Type: Single Family For Sale
Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishe...
523 North Main Street
Woodbury, Connecticut 06798
$990,000 | Under Contract
3 Beds | 2 Baths | 2300 Sqft | 2.1 Acres | 149 Days on Market
Property Type: Single Family For Sale
To be built Modern style home with gorgeous southern views and privacy from your neighbors. Enjoy the wall of glass overlooking a bluestone patio, and beautiful views above Main Street North! Just a few minutes from Woodburys town center, this home provides an open floor with a k...